


Hot for Teacher

by CS_impala67



Category: Supernatural
Genre: Anal Fingering, Angst with a Happy Ending, Bottom Dean Winchester, College | University Student Dean Winchester, Coming Out, Dean Winchester's First Time With a Man, Eventual Smut, First Kiss, First Time, Fluff and Smut, Gay Castiel (Supernatural), Gay Dean Winchester, Getting Together, Good Parent John Winchester, Happy Ending, Light Angst, M/M, Masturbation, Mutual Pining, NSFW Art, Parent Castiel (Supernatural), Rimming, Single Parent Castiel (Supernatural), Teacher Dean Winchester, Top Castiel/Bottom Dean Winchester, Virgin Dean Winchester
Language: English
Status: Completed
Published: 2020-10-16
Updated: 2020-11-10
Packaged: 2021-03-09 06:13:42
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 20
Words: 35,275
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27049993
Author URL: https://archiveofourown.org/users/CS_impala67/pseuds/CS_impala67
Summary: At the yearly summer carnival that he brings his daughter to, Cas meets a young man that takes his breath away. Beautiful, slim and with a sort of 'twink' look, Cas can't help but stare, especially at the way the man's shirt clings to his body after he climbs out of the dunk tank. Cas just shakes it of, it's not like he'd ever see the man again right? Right?He puts the gorgeous man out of his mind, until he walks in to pick up his daughter from school on the first day and who does he see? Of course Dean ends up being his daughter's student teacher. Of freaking course. What are the chances. seriously? Life just got a whole lot more interesting.
Relationships: Castiel/Dean Winchester, John Winchester/Mary Winchester
Comments: 171
Kudos: 472





	1. Chapter 1

**Author's Note:**

> I originally intended to enter DCBB, but I wasn't able to write this in time. Its all plotted out already. I will be posting a new every chapter at least once a week. Hope you enjoy!

Castiel stood in front of the coffee maker in his kitchen, willing it to drip faster. He had a rough night sleep, and still had a long day ahead of him. The Annual Children’s Carnival was today. It was an Event that St. Joseph's College threw every July and Castiel made sure to bring his daughter to each year. It was something she talked about all year, and seeing the smile on her face was worth the headache of the hordes of children he would have to endure.

He sighed as he poured the coffee into his mug once it was finally done brewing. The first sip was always the best. It was probably all in his head, but once he took that first sip of his morning coffee, he always felt a little more awake; like he could take on the day. And this morning he desperately needed it, because he already could not wait to go to bed.

He made his way up the stairs and down the hallway till he reached his daughter's room. He knocked on her door. “Bianca, are you almost ready?” He called through the door.

“Almost Papa!” She yelled back.

“Ok sweetheart. Hurry up so we can get there on time.” He replied before he turned and walked back downstairs. He grabbed his keys and wallet from the basket by the door as he waited for her to come down. One thing he learned very early on as a parent was that he would most likely be late to everything now that he had a kid. The first few years were the hardest though. He had only been 22 when Bianca was born. She was the result of a one-night stand.

It had been New Year’s Eve and his friends had pressured him to go to the party that the most popular fraternity was throwing. He had always been accused as being a stick-in-the-mud, so he went just to appease them. He ended up drinking much more than he has originally planned. His friend Meg had somehow convinced him that it would be a great idea if they ‘hooked up’ as she said. What ended up happening was probably one of the most awkward sexual encounters in existence. It also cemented the fact that he was definitely 100% gay. Two months after that, Meg had come to him crying that she was pregnant. She didn’t want to keep the baby and was planning on putting it up for adoption. She only told him because he was the father. He was terrified at the thought of having a kid. But he was even more sick at the thought of giving his own child up. He begged Meg to give him custody of their child.

Once she gave birth to their daughter, Meg signed over her parental rights to Castiel and then disappeared from their lives, leaving him to raise a newborn alone. He didn’t even have any help from his parents because once they found out that, not only was he gay, he had a child out of wedlock as well, they disowned him completely. If it wasn’t for his older brother Gabriel, who took him in and helped him those first few years, he didn’t know what he would have done. He had only just graduated college a few months before she was born and he had yet to find a job in his field at the time. He would have been homeless on the streets if it wasn’t for Gabriel. Gabriel could be a total pain in the ass, but he came through when he needed him most and was there for him when no-one else was. Now, 8 years later, Castiel was 30, had a successful career as a computer programmer, owned his own home, and had an exceptional daughter that he would do anything for. Gabriel was still in their lives as a doting uncle and lived close enough that they saw him at least once a week. It was still a struggle being a single father, but Castiel was in a fairly good place in his life now. The only thing missing was a partner to share it with. But that was not a priority now, his daughter was.

He was drawn out of his internal thoughts when he heard his daughter stomping down the steps. “What have I told you about running down the stairs Bee?” He asked sternly as his daughter came down.

‘’ Sorry Papa, I forgot.” She smiled sweetly. Castiel knew it was her ‘get out of trouble smile’ that she somehow perfected. He rolled his eyes, but his lips twitched into a smile. He had a hard time ever staying upset with her. He could only imagine how she would eventually exploit that in her teenage years.

“Come on Bee, lets get going.” He chuckled as he steered Bianca to the car. He pulled out of the driveway of their two-story home in West Babylon, and made their way to the college Campus in Patchogue. On the way he appreciated the beautiful view. He was glad they lived on Long Island, New York. It was not cheap, but it was definitely pretty and scenic.

Once they arrived, he led his daughter to the entrance where they waited in line and paid their entrance fee, which was really just a $20 donation to the early child education program. He was happy to pay the donation because he fully supported anyone who wanted to educate the youth. They were given wrist bands to enter once he paid and Bianca was jumping up and down excited the entire time. She had a huge smile on her face before they even reached the first activity. Castiel was again glad that he could put that smile on her face. He always worried that he couldn’t be enough for her as a single father. So, times like this definitely made him feel like a good father. It was days like this that made all of the struggles as a single parent worth it.

He let Bianca drag him to a few rides she wanted to go on. The roller coaster was her favorite and he endured it for her sake. Then they made their way to the face painting booth where she had the artist paint a bee on her cheek. Castiel lit up inside because he was the one who gave her the nickname of Bee because of her name as Bianca, as well as his love of bees (he might have named her Bianca simply because it could be shortened to Bee. But he would never admit to that.)

They eventually stopped for lunch before slowly making their way through more of the carnival. Eventually they made their way to the dunk tank. Bianca wanted to try so they waited on line for their turn.

When it was finally her turn, they both stepped up and the young lady running the booth handed Bianca three balls. “Hey little lady! My name is Charlie. They are just changing over who sits in the booth. So, it will just take a minute. What’s your name?” she asked.

“My name is Bianca. But my papa calls me Bee.” His daughter said enthusiastically. Castiel was slightly distracted though. He watched the person in the tank switch spots with a new young man. His breath caught in his throat. He couldn’t see much from this far back, but the new guy was beautiful. He looked to be about 20, and sort of ‘twinky’ which Castiel had never admitted to anyone before, but was a kink of his. The young man was slim but fit too. He had full lips that were stretched into a smile as he settled into his spot on the board above the tank. The young man was looking at Castiel’s daughter who was getting ready to throw the first ball.

“Come on Sweetheart, knock me down. I could use a dunk in the water. Its so hot out here!” The young man called out. Bianca smiled and threw her first ball, completely missing the target. She pouted.

“That’s okay little lady. You still have two more left. You can do it!” The young man encouraged Bianca. She threw her second ball and missed again. She was getting very discouraged.

The young lady, Charlie, leaned into their space and whispered to Bianca, “That guy in the tank is my best friend Dean. I really want you to dunk him. Do you think you can do that for me Bianca?” she asked.

“Ugh Charlie, I’ve been trying. You saw me, right?” his daughter responded. He had to hold back his chuckle. This was too cute of an exchange.

“I did see. Do you know what I think you should do Bianca?” Charlie asked.

“What?” his daughter asked excitedly.

“I want you to take your last ball and run up and smack it into the target to dunk my friend Dean. Can you do that?” Charlie asked.

“Is that allowed?” Bianca asked, scared she would do something wrong.

“I’m in charge of this booth and I say it allowed. So, can you do that for me Bianca?” Charlie smiled.

He saw his daughter’s eyes light up mischievously, and then she ran as hard as she could and smacked her ball right on the target which dumped Dean into the tank. Dean spluttered before he came up.

“That was dirty Charlie! Getting a young child to do your dirty work!” He yelled out to Charlie. Castiel could tell that he was only playfully glaring though. Dean began to climb out of the tank and Castiel became mesmerized at the way his white tank clung to his body and became almost see-through, showing off his pecks and abs. Castiel felt his mouth go dry and his pants tighten slightly as he watched Dean’s pants hang low on his hips and a sliver of skin show on his body. Cas looked quickly away from Deans body before he could be accused of checking him out. This was totally not a venue that he should be having these thoughts at.

“I got him Papa!” Bianca yelled as she ran back to Castiel’s side.

“You sure did sweetheart.” He smiled at her.

“Great job Bianca!” Charlie squeaked. “Give me a high five!” she said and Bianca was happy to comply.

“Papa, can we go on the Ferris wheel now?” Bianca asked him.

“Of course, Love, let’s go.” Castiel replied. He thanked Charlie and began to walk towards the Ferris wheel. He turned his head, trying to get one last glimpse of the young man, Dean. He found him staring back. They locked eyes and Castiel felt like something profound seemed to pass in their gaze. He shook himself out of that as he chastised himself for such a silly thought. It was probably just because it had been years since he had more than just his right hand keeping him company. That had to be all it was. He tried to put the whole encounter out of his head as he followed his daughter through the carnival for the rest of the day. It wasn’t like he would even see Dean again.


	2. Chapter 2

Dean watched the man and his daughter walk away. He could not stop staring after them. When they had locked eyes, Dean had been struck speechless. Even from a distance, he could see how ridiculously blue the man’s eyes were, and how full and soft his lips looked. His hair had that slightly messy look that screamed, just fucked. It was giving Dean all sorts of ideas. He looked older than Dean too, probably at least 30. Just his type. Dean had always felt an attraction to older men. Not that he’d ever acted on said attraction, being a 22-year-old gay virgin. Plus, he was still in the closet. Charlie was the only person in his life who knew he was gay. That didn’t mean he didn’t fantasize though.

He was so lost in thought that he never saw the next kid in line throw the ball and before he even realized what happened, he found himself under water again. He quickly re-surfaced, coughing up water he had inadvertently breathed in from not paying attention.

“Get your head out of the clouds Winchester!” Charlie shouted at him laughing. She probably knew exactly what had been going through his head.

“Yeah Yeah, Charles.” He grumbled back, blushing, as he climbed back up onto his seat above the tank. He pushed thoughts of the older man out of his head and tried to focus on the kids at the booth to avoid another lung full of water. The last thing he needed was to drown in a damn dunk tank because he was thinking with his downstairs brain. He most likely would never see the other man again anyway, and even if he did, its not like Dean would have a shot. The man was most likely straight. Plus, Dean was a 22-year-old closeted gay virgin. Not really much of a catch. So, he shook himself out of those thoughts and spent the rest of his time in the tank not thinking about those blue eyes.

Once the carnival was over, he climbed out of the tank and walked over to where Charlie was waiting for him. They planned on going out for dinner after the Carnival.

“You look like a drowned rat.” She laughed at him. That was not entirely inaccurate. His clothes and hair were soaked. He hadn’t originally planned to be in the dunk tank, so he wasn’t wearing a bathing suit. He just had on a pair of denim shorts and a white tank. Luckily, he had brought a change of clothes in his car because he had planned on changing before they went to eat anyway.

“Thanks Red.” He rolled his eyes at her. “Let me just grab my change of clothes and get dressed and then we can head out to the diner.” They began walking towards the parking lot where he got his clothes and went to get changed really quick. He made his way back to his car, a beautiful ‘67 impala that his father had gifted him when he graduated high school. It was definitely his most prized possession. They drove to the Terrace Diner, which was their usual hang out spot. They went in and were seated quickly. Once the waitress had taken their orders, Charlie cleared her throat and Dean looked up at her.

“So…. are we gonna talk about Mr. Dreamboat?” She asked with a smirk.

“Dunno what you’re talking about Red.” He deflected, praying he wasn’t blushing too bad.

“Oh, don’t give me that crap Dean. I saw the way you looked at him. And you were so distracted you almost drowned.” She said pointedly. “Plus, he’s exactly your type.” She added.

“How would you even know what my type is Charlie?” He huffed.

“Dude! You totally love the appeal of older men with scruff and dark hair! Harrison Ford? Dr. Sexy?” She accused.

“Ugh fine. Yes, I found him attractive. Not a big deal. Not like it matters anyway.” He grumbled as he sank down in his seat. “It’s not like I’m ever gonna see him again. And even if I did, I highly doubt I’m his type.” He muttered self-deprecatingly.

“You don’t know that Dean!” She argued.

“He’s probably straight first off. Plus, why would someone like him want a 22 year old virgin. Just forget it Red. Its not like I even plan on dating right now anyway. I’m still in the damn closet for Christ’s sake!” He argued back.

“You know, I think if you came out to your family, I’m pretty sure they will all support you Dean.” She said compassionately.

“I don’t know Red. I mean, my mom will probably be fine with it. And Sammy too. But my dad? He’s who I’m worried about.” He said as he rubbed his hand down his face.

“Well, whenever you decide to come out to other people, you know I have your back.”  
He smiled. Charlie was the best friend he could ever have. “Thanks Charlie.”

They ate their food and then he dropped her off before making his way home. He walked inside and said hello to his parents, who were watching a movie in the living room, before making his way up to his room. He was exhausted after the long day at the Carnival so he quickly got ready for bed and slipped under his sheets. He drifted to sleep with thoughts of blue eyes and full lips.

*******************************************

The rest of July and August passed quickly, and before he knew it, it was September and he was walking into John F. Kennedy Elementary School for his first day of student teaching. It was his last requirement for his degree and then he could get his teaching certificate. He walked to the main office to sign in and get his class placement, before making his was down the hallway to the third-grade classroom he would be at from now till December. He made sure to get there early so he could meet the teacher and settle in before the students arrived.

When he walked in, there was a heavy-set black woman writing on the board. She turned to him with a smile when she heard him come in. “You must be Mr. Winchester.” She said cheerfully as she held her hand out “I’m Missouri Moseley.”

Dean shook her hand “Nice to meet you Miss Moseley. You can call me Dean.” He said nervously. She seemed friendly and had a soothing southern accent. He was just nervous about his first day.

“No need to be nervous, Sugar. Let’s get you settled in and go over a few things before the class comes in." She walked him over to her desk where she gave him his own drawer for anything, he might need it for. She went over the daily schedule and gave him a brief review of what they would be doing this first week. As she was finishing, they could hear students making their way down the hallway towards their classrooms. Dean followed her to the front of the class as kids began trickling in.

“Welcome children! Please find the desk with your name on it and put away your supplies in your desk. Once you do that, hang your backpacks on the hooks on the left wall and place any lunch bags on the table underneath them. Then please come back to your seats and we will all introduce ourselves.” Missouri stated and then there was a quick flurry of activity as the children followed her directions.

“First day is always a little chaotic.” She laughed at the deer in headlights look on Dean’s face. Once the class was settled down again, Missouri got their attention.

“Good morning everyone! My name is Miss Moseley and I will be your teacher this year. This young man next to me will be my assistant teacher until December. His name is Mr. Winchester. Now we are going to go ahead and go around the room and I want you each to say your first and last name and something fun you did this summer. Let’s start with you.” She pointed to a girl in the first row.

“My name is Amanda Winters and this summer I went to Disney!” She said excitedly.

“Very nice Amanda. Ok, now you child.” She pointed to the next kid. They went around the room and all introduced themselves and were excited to talk about their summers. Eventually it was the last kid’s turn and Dean turned to face her. She looked familiar to him, but he couldn’t place where he knew her from.

“My name is Bianca Novak. Something fun I did this summer was make Mr. Winchester fall into the dunk tank at the Carnival.” She smiled with a glint in her eye.

‘Fuck!’ was all Dean thought as he realized where he recognized her from, and the color drained from his face. Blue eye’s daughter was in the class he was going to be student teaching in for the next three months. He was bound to run into her father at some point. This semester was definitely going to be interesting.


	3. Chapter 3

Castiel had been nervous all day, barely getting any work done on the website he was currently designing for one of his clients. Today was Bianca’s first day of third grade, and like every year before this one, he was a basket case. He always worried the first day, wondering if his daughter would be blessed with a nice teacher or not, and if she would end up in a class with at least one of her friends. It was just one of the many worries he juggled as a parent.

He had glanced at the clock all day, willing it to move faster so that he could pick Bianca up and ask her about her day. Then, maybe he could finally relax and make headway on this website. Luckily, the client wanted something easy and simple, so it shouldn’t take long, once he could really put his head to it. He sighed as he glanced back up at the clock, noting he still had an hour before he had to pick his daughter up. Deciding he may as well stop pretending to work on his project, he collected his wallet and keys, and made his was out to his car. He drove down to main street and decided to stop at the 7-Eleven to grab a cup of coffee and a doughnut to eat in his car while he counted down the minutes until three o’clock.

He parked in the lot and shut off the ignition, before exiting his car to make his way into the convenience store. Since his daughter’s school was just up the block, this place was pretty convenient. He walked up to the coffee counter and fixed himself a large cup just how he liked it; Heavy on the sugar and light on the cream. He took a sip to make sure it was perfect as he perused the pastry aisle, debating what to get. Did he want a doughnut? Or maybe he wanted a danish. He couldn’t decide, so he just grabbed one of each, making sure to also grab one of the pink frosted ones for Bianca. He figured it would either work as a celebratory treat if she had a good day, or a consolation to cheer her up if it had been a bad one.

He took his items up to the cash register, and he noticed the red-headed cashier. She looked familiar but he couldn’t seem to place where he knew her from. As he placed his items on the counter, the young woman looked up and smiled at him.

“Hey! I remember you!” She beamed cheerfully. “You were at the fair this summer with your daughter, Bianca, if I remember her name right.”

Castiel’s own face lit up in recognition, realizing now, exactly why she looked familiar. She was the young woman from the carnival dunk tank booth who had conspired with his daughter to dunk that young man.

“I thought you looked familiar.” He said politely. “I’m Castiel. I’m sorry I don’t remember your name though.” He continued apologetically.

“No worries! The name’s Charlie.” She smiled, waving off his apology. “How is your daughter doing? She was absolutely adorable!” She exclaimed perkily.

“She’s doing well. I’m actually on my way to go pick her up from school.” He told her. “I’m really hoping she had a good day. I always worry.” He confessed.

“I’m sure she did. Does she um…does she go to J.F.K. elementary down the road?” She asked curiously.

“That she does.” He affirmed. Charlie then got this weird look on her face and just hummed in reply before ringing Cas up. He paid for his items and thanked her before wishing her a good day.

“You too Castiel. And don’t worry, I’m sure you will be pleasantly surprised when you pick your daughter up.” Charlie said mysteriously, with a suspicious glint in her eye that confused the hell out of him. He left the store and shook off the weird interaction, as he started his car and made his way to the school a couple of blocks north.

When he pulled into a spot, he checked the time, noting that he still had 15 minutes until dismissal, so he pulled out his phone to get some work done. As he checked his emails and responded to the urgent ones in his inbox, he sipped his coffee and ate the danish he picked out. As three o’clock hit, he got out of his car and shut the door behind him, before making his way into the building and showing his license to the lady at the front desk. He stood in the lobby with the other parents, waiting for his daughter's teacher to walk the students who were walkers, down the hall to hand them off. He saw a middle-aged black woman walking down the hall with a young man behind her, being followed by a handful of students. He was pretty sure the woman was his daughter's teacher, and as the group came closer, he could see he had been right, when he saw Bianca with them. He noticed her face had a huge smile on it, and his worry began to dissipate, now that she seemed happy. She must have had a good day then, he reasoned. As the group reached the throng of parents, Bianca ran to him and threw her arms around his waist.

“Papa! Papa!” she yelled excitedly. “Look who's here! It's the man from the dunk take, Mr. Winchester.” Cas was confused for a second, before he looked up from his daughter's face, and that's when he saw him; The gorgeous, green-eyed twink that had captured his breath over the summer. He was so speechless from the surprise of seeing the young man again, that he just stared slack-jawed like an idiot before the man _, Mr. Winchester_ , cleared his throat.

“Ahem.... You must be Mr. Novak.” The man said, as he held his hand out for Cas to shake, causing the older man to shake himself out of his stupor to take the younger man's hand in his. As they touched, Cas felt a spark fly between them.

“Yes... Um… Yes, I'm Mr. Novak, Bianca's father. You can call me Cas though. My uh, my first name is Castiel. And you are Mr. Winchester?” He stuttered, face blushing as he did so.

“Yeah, but you can call me Dean.” The man smiled, his gorgeous white teeth on display.

“Dean it is then. I'm, uh, I'm surprised to see you here. I thought you were a student volunteer this summer at the fair when you were in the dunk tank.” He probed further; voice laced with confusion.

“Oh yes, heh… Your daughter made sure to remind me all about how she dunked me that day.” Dean chuckled, hand going to rub the back of his neck. “I um… I am a student, I'm, uh, actually student teaching this semester here in miss Moseley’s class. So… I guess we'll be seeing each other a lot.” Dean explained with a shy smile. They locked eyes and stared each other way longer than was socially acceptable, before Bianca pulled on his sleeve to get his attention. He broke eye contact to look down at his daughter.

“Papa, come on! I want to go home!” She whined tiredly, likely exhausted once the excitement of the first day began to wear off.

“Of course, Bee.” He told her, before looking back up at Dean. “It was nice to see you again Dean. I better get my daughter home before she has my head.” Cas joked lamely. Dean chuckled back awkwardly.

“Yeah, okay. Uh…see around Cas.” They smiled shyly at each other before Cas took Bianca's hand and walked her out.

All through dinner that night, as Bianca chatted about her day, Cas couldn't help but inwardly cringe at the awkward encounter with Dean. He had never thought he would see the young man again. Then _of course_ , when he finally does, Cas acted like a bumbling teenager with a crush, instead of the thirty-year-old man that he was. And now he would have to see the young man every day at pickup.

He was still beating himself up over it when he finally slipped into bed that night. As he lay there though, his thoughts started to turn towards how he remembered Dean at the fair, when he climbed out of the water, and his tight white tank had clung to his tone body. Before he could stop himself, Cas’ hand slipped down his stomach and beneath the waistband of his pj's, before wrapping around his slowly hardening cock. He began stroking himself as he thought of Dean’s body in that wet tee. He came with the young man's name on his lips, and as his breathing returned to normal, all he could think of, was how much more awkward he was going to feel the next time he saw a Dean, after getting off to thoughts of his young fit body. Fuck! He was royally screwed.


	4. Chapter 4

Dean watched Mr. Novak- _Castiel-_ walk out of the school with his daughter, his brain still reeling from seeing him again. Over the past two months since the Carnival, he had convinced himself that he had imagined just how sexy the other man was; That is mind must have over-exaggerated just how blue his eyes had been, that is jaw wasn't really that chiseled, and that his hair wasn't really that sexy. But nope, he definitely hadn't remembered wrong. Castiel still looked like a Greek god; Features so perfect, they could have been chiseled in stone. The fact that the dude turned out to be kind of dorky and awkward, only made him that much more attractive to Dean. What grown man still blushed like that talking to a teacher? An adorable one, that’s who.

The rest of the pickup went by in a blur, and soon he was walking back to the classroom with Miss Mosely so they could pack up and leave, first day successfully down. He was so lost in thoughts of the other man still, as he packed up his bag, that he didn't hear his name being called, until he felt a firm nudge in his side.

“What?” He asked distractedly.

“Boy! Your head must be so far up in them clouds. I called your name five times and you ain't heard a one.” Missouri tutted at him; eyebrow raised in reprimand.

“Sorry… I, uh…it’s just… it's been a long day. Just thinking about class tomorrow.” He lied quickly, trying to school his features into something believable.

“Boy, don't you be lying to me. I can sniff out a lie a mile away. Don't think I couldn't see what went on between you and that Castiel fella.” She chastised the younger man, clearly not believing his lie for a second.

Dean stomach sank, and his heart beat fast. Had he been that obvious? He wasn't _out_. He _couldn't_ be out right now; He wasn't ready. And at _work_? He knew what could happen to a male teacher if parents found out he bat for the other team. He was only student teaching and he’d be gone before he even begun his career! He must have been broadcasting his panic loudly on his face, because he felt a warm hand rest on his shaking shoulder.

“Sugar, don't you be fretting. I got no plans to be outin’ you boy. Whoever catches your fancy makes no difference to me. Your secret's safe, honey.” Her sweet southern voice reassured him, and he felt his body begin to relax.

“Thanks Missouri. I’m...uh…I’m not exactly out yet. I don't plan to be anytime soon.” He confessed quietly, tension leaving his body as the admitted out loud to the second person ever, that he wasn't straight. A small weight was lifted, knowing another person knew and didn't seem to be judging him.

“No worries honey. I won't tell a soul.” She promised with a smile, before turning a serious gaze his way. “Just a warning though, dear. I'd suggest you wait till you finish your semester here before you go hitting on one of the parents.”

Dean scoffed “You don't have to worry about that ma’am. He's way out of my league to start with. And I highly doubt he even swings my way. Dude’s probably straight.”

“Hm…You never know.” She argued. “Just keep it in your pants till December 25th.” She smirked, making Dean chuckle.

“Yes ma'am.”

They both grabbed their coats and walked out of the classroom, switching the lights off behind them as they left, before they made their way to their cars. They wished each other a nice night and Dean climbed in Baby before pulling his cell phone out. He scrolled through his contacts till he got to Charlie's name and opened their chat to send her a text.

**_Dean: Hey Red. Want to grab a bite at the Roadhouse?_ **

He didn't have to wait long for a response.

**_Charlie: Absolutely! I've been craving fries all day, it's like you read my mind!_ **

**_Dean: Awesome. meet you there in 20._ **

**_Charlie_ ** **😊**

He pocketed his phone and turned his key in the ignition, before pulling out of the spot and making the 15-minute drive to the restaurant. It was a bit of a run-down, family style place that served burgers and similar type of food, and had a bar in the corner. It had always been one of his favorite places to eat, especially since the owner Ellen was a long-time friend of his mom's. He pulled into the parking lot and shut off the car before making his way inside. He waved hello to the bartender as he made his way to the booth in the back corner- his regular spot. He’d been coming there so long, that he never had to wait to be seated, he was basically family anyway.

Since he arrived before Charlie, he flagged down the waitress and ordered himself a beer, slowly sipping it as he waited for his best friend to show.

“Hey Handmaiden!” Charlie greeted him cheerfully, as she plopped herself down across from him in the booth. He rolled his eyes at the greeting; annoyed she was still calling him that stupid nickname. One time- _one time-_ he LARPed with her, and it had been the only spot open. Of course, Charlie insisted on calling him that now every time she saw him, even two years later.

“I told you to stop calling me that.” He grumbled, with no real heat, at a familiar routine.

“Yeah, yeah.” She waved her hand dismissively, like she did every time he complained. “So… how was your first day?” She asked, after the waitress delivered her drink. It was some fruity abomination that Dean turned his nose up at, before he slumped down over the table. “Ugh, it was mostly fine. Kids were hyper but no real troublemakers so far. They're freaking _exhausting_ though.” he complained.

“I bet.” She said as she sipped her drink, before looking up at him with a glint of mischief in her eyes. Uh-oh. Dean did not like that look. “Soooo… run into anyone interesting today?” She asked, her innocent look clearly fake. “Maybe someone handsome, who's tall, dark-haired, with bright blue eyes perhaps?”

“ _How the hell did you know that!”_ He hissed. “It didn't even happen an hour ago, and I didn't tell anyone either, so unless you somehow are now sharing secrets with Miss Mosley, I have no idea how you found out.”

“First of all, I have no idea who Miss Mosely is, but Mr. Dreamboat stopped in the store before he headed to school to pick up his daughter. I figured you’d probably see him at pick up.” she smirked “I bet you were swooning when you saw him.” She batted her eyelashes obnoxiously, before laughing to herself.

“Ha.Ha.” He deadpanned, unamused at her teasing. “But yeah, I did run into him. And I'll be seeing a whole lot of him for the next three months since Bianca is in my class. _Charlie_ … what am I going to do?” He whined, as he banged his head against the table miserably.

“Dude, don't be such a drama queen. This is a good thing! You’ll get to see your crush everyday now.”

“Yeah and I get to be reminded on a daily basis that he's so far out of my league, we aren't even playing the same sport. Plus, like I said last time, dude’s probably straight. It's not like I'd ever stand a chance.”

“You never know…” She shrugged. Why did everyone keep saying that today? He didn't want to keep talking about Cas, so he changed the subject, and steered the conversation onto other topics as they ate their meals. The rest of the conversation was much better, and by the time they paid their checks, and went their separate ways, Dean’s thoughts were no longer on the gorgeous man.

When he got home, he greeted his parents who asked how his day went. He talked to them for a bit, before retiring to his room for the night, ready to sleep after the exhaustion of his day. But as he slipped under the covers, his mind couldn't help but picture blue eyes and plush lips, and before he knew it, his hand was wrapped around his dick. It took no time at all for him to come, Castiel's name on his lips, as he painted his stomach white with his release. This semester was definitely going to suck. How was he going to be able to look at Cas every day, pining after the man that wouldn't ever even _think_ of giving him the time of day?


	5. Chapter 5

The rest of the week of school went about the same as the first day. Cas sent Bianca off on the bus each day, before coming back home to work in his home office. At least he was finally able to concentrate a bit more on his client’s website, now that he knew his daughter was in good hands and he didn’t have to worry so much about her. Unfortunately, he often found his thoughts drifting to one particular green-eyed young man. No matter how much he tried, he couldn’t help but picture that damn wet tank top clinging to his perfect frame. His hand had been getting a lot of action the last few nights.

Luckily today was Friday, so after pick up in the afternoon, he wouldn’t have to see Dean for the next two days. Hopefully, a few days away from the young man would lessen Cas’ lust filled thoughts. It was a bit ridiculous that he was in his thirties and nursing a school girl crush on another man. It had been a long time since he felt an attraction like this to anyone, much less someone so much younger than himself.

He sighed as he rubbed the tension out of the bridge of his nose, before sending the images of the website to his client. Hopefully they would accept them and then he could finish the few details he had left before making the site go live. Then he could move on to the next client. At least that one would be more exciting and hopefully hold his attention better. It was a site for a local Honeybee farm after all, and it was something that greatly interested him.

He stood up and stretched the kinks from his back, before he made his way from his office to his kitchen to grab a bottle of water. He glanced at the clock and realized it was later than he thought, and he needed to pick Bee up in an hour. He chugged the water and grabbed his keys, deciding he would stop at the convenience store again, before he went to the school. He needed a pick-me-up, and he was becoming addicted to the danishes the store sold. The cheery red-head, Charlie also helped brighten his moods. It was impossible to be around that woman and not have some of her energy rub off.

He drove to the store, locking his car before making his way inside. He picked out a raspberry danish this time, and made his way up to the counter.

“Hey Cas! How’s it going today?” Charlie asked, her usual bubbly self, making Cas smile.

“Hello Charlie. Things are alright. Thank God it’s Friday though. I’m exhausted.” He lamented, making her chuckle.

“I hear ya. Luckily, I’m off this weekend so I can go LARPing. I can’t wait.” She told him.

“LARPing? I’m sorry, I have no idea what that is.” He apologized, having never heard of that term before.

“Oh man, it’s awesome! It stands for Live-Action-Role-Playing. Soooooo much fun. We dress up as our characters and act out the story. I’m queen of Moondoor!” She explained, voice clearly excited as she babbled about it. Cas was still unsure what exactly it was but it seemed to be something she enjoyed.

“Sounds like a good time.” He said politely.

“Its awesome. I keep trying to get Dean to come back and LARP with me. He was such a great handmaiden.” She sighed wistfully. Cas chuckled. He couldn’t really picture Dean doing something like that; something so… _nerdy_ , for lack of a better term. Dean seemed more like the type of guy who was popular in school; probably a jock. Definitely much higher on the social ladder than Cas had ever been. His high school days had revolved around Math Club and robotics. He had been the quintessential nerd in High school.

“Well, it was nice to see you again Charlie. I’m off to go pick up Bianca now. Have a nice weekend with your LARPing thing.”

“Thanks! Catch ya later Cas!” she waved him goodbye.

He made his way to the school and walked in the building to stand with the other parent’s again like usual, scrolling on his phone through his emails as he waited. A few minutes later, Bianca’s class was being led down the hall by Dean. Cas felt his palms sweat when he caught sight of the other man. _Stupid damn crush_. He really had to have a talk with his body about its reactions to this man. It was becoming ridiculous.

“Heya Cas!” Dean beamed when the class reached where the parents were waiting.

“Hello, Dean.” Cas said loudly, trying to be heard over the raucous of the kids around him.

“Thank God it’s Friday, right?” The other man chuckled and Cas nodded in agreement as their gaze locked on one another; Green eyes drawing him in. He almost forgot where he was for a minute, until he overheard one of the kids in the lobby near him misquoting one of his favorite movies.

“ _Luke…ksh… I am your Father…ksh_.” A young boy said, trying to mimic Darth Vader’s deep, heavy mechanical breathing. Cas just scoffed to himself.

“No one ever gets that line right.” He complained out loud to no one particular. One of his biggest pet peeves were misquoted lines, especially from his favorite movies. He didn’t understand how so many people always misquoted an iconic line like that. It truly baffled him.

“Dude! Right?” Dean exclaimed in agreement. “I don’t get how everyone always says that one wrong. Its not _Luke I am your Father_. Its _No… I Am your father._ How hard is it to get it right?” he waved his hands around in a clearly annoyed gesture. Cas was a bit stunned. He’d never met someone as passionate as he was about that particular thing.

“Are you a Star Wars Fan?” He asked Dean curiously, surprised because he still didn’t picture the other man as liking anything remotely like that. Dean seemed like more of an action movie type of guy.

“Am I a **_Star Wars Fan_**? Am **_I_** a Star Wars Fan?” He squawked indignantly. “Dude understatement. They are my favorite trilogy of movies!”

“Mine too!” Cas replied excitedly. He didn’t have many friends, and the few he did have, did not share his taste in movies or tv shows at all. And for Dean, of all people, to share his interests? Damn, this was going to be even harder to reel in his crush now.

“No Way! I definitely wouldn’t have pegged you for a fan Cas. You do not seem like the type of guy to like nerdy things.” Dean spoke, mirroring Cas own thoughts.

“I could say the same for you Dean.” He argued back.

“Touché”

By this point, Bianca had started tugging on Cas’ sleeve, clearly not caring that her father was having a _moment_ here.

“Well I need to be getting my little girl home. It was nice talking to you Dean. Have a great weekend/” He told the other man sincerely.

“You too Cas. See you on Monday.” Dean smiled back as Cas turned to make his way out of the building.

“Papa, can we go to Wendy’s for dinner? You said if I had a good week in school we could. Please, please, please!” His daughter begged excitedly. He did promise her after all.

“Of Course, Bee. There is one right up the block. Maybe when we get home, we can put on that new movie you wanted to watch too.” He offered, making Bianca light up.

“Yes! The Pony Movie!” She beamed and Cas chuckled fondly as they buckled up and made the short drive to the restaurant.

The rest of the night, he replayed his conversation with Dean over in his head, smiling as he remembered how passionately Dean had agreed with him. He was still surprised at finding out the few nerdy things he now knew about the younger man. He wondered what else they had in common? He figured he had plenty of time to find out when he saw the man each afternoon. Where he initially dreaded the thought of having to see Dean every day, now that he knew they had some things in common, maybe it wouldn’t be so bad. He could at least make friends with the man, even if he couldn’t have him the way he wanted. Something was better than nothing after all.


	6. Chapter 6

September and October flew by before Dean knew it, and suddenly it was Halloween already. He had finally gotten into the swing of things in the classroom, and he fell in love with most of his students- _little Jimmy could go suck an egg though, the little brat_. His students all seemed to like him too. It was always “Mr. Winchester _this_ ” or “Mr. Winchester _that_ ”. They all seemed to gravitate to him, even more so than Miss Moseley, which she teased him about constantly. She didn’t seem to mind either, _“The more they bother you Sugar, the less they bother me.”_ She always joked whenever they hounded him.

He didn’t intend for it to happen, but he ended up becoming really attached to Bianca, and it honestly had nothing to do with who her father was either. The girl was smart as a whip and funny as hell too. There were a number of times where Dean had to turn his head to hide his laugh at some of the things that came out of her mouth.

One-time Dean had been drinking a bottle of water as they left the classroom and Bianca told him to make sure he didn’t drink it in the car because you should never drink and drive. Cas had been there for that one and Dean had watched him try to explain that that was only for grown up drinks. Bianca’s response to that had been “Oh! Like what you drink at night when I give you a headache!” Cas had turned bright red and Dean had laughed so hard at Cas stammering and quickly guiding Bianca out of the school.

She had also referred to her classmate Jimmy as an assbutt- which Dean absolutely agreed with but couldn’t tell her that. Dean had had to tell her Dad about it, since profanity was not allowed in school, even if little Jimmy _was_ an assbutt. Cas had apologized profusely, scolding his daughter who just said “But Daddy! You call Uncle Gabe that all the time!” Cas had again blushed as he dragged his daughter out of the school again, muttering to himself as he went.

Both men had also gotten much friendlier with each other over the last two months as well; first bonding over their shared love of Star Wars, and then delving into different topics they both enjoyed, such as baking. It was slow going though, since they only had about two minutes to talk every day at pick up, so their conversations were pretty superficial, not really getting into anything personal. But it was still nice to just be able to see the other man’s gorgeous face every afternoon. It gave him something to look forward to each day.

The class had a Halloween Party and they all dressed up; Dean dressed as Han Solo of course. The kids were all adorable in their costumes as well. Bianca was definitely his favorite. She had come in in the most adorable Bumblebee costume, and that’s when he found out the real reason her nickname was Bee. She had proudly informed him that her papa loved bees and that’s why he named her that, before asking him if he liked her costume. He had told her of course he did, and then she proceeded to run around the room trying to sting all of her classmates. It was never a dull moment with these kids.

At pick up that day, Cas had even complimented him on his choice of costumes, making Dean blush this time, as he stammered out a thank you. It had been a pretty good day, and if he happened to have some _alone time_ that night, thinking about Cas telling him how good he looked, well, no one had to know.

***************

November and December passed much the same way September and October had; fast and in the blink of an eye. His daily short chats with Cas being the highlight of most of his days. It was already December 23rd and it would be Dean’s last day student teaching. He would be sad to leave and not see these kids anymore. But if he was being honest with himself, the thing he was going to miss the most was seeing the gorgeous blue-eyed man every day. After today, he would probably never see Cas again.

Miss Moseley had bought a cake for him and the class had all gave him hugs-a few kids even cried- and they all told him how much they would miss him. When the end of the day arrived, and he walked the student’s out to meet their parents, he had to plaster on a fake smile, so no one would know just how much it was killing him that this was his last day. It must not have been too convincing though because Cas took one look at him, and his brow pinched in concern.

“Hello Dean. Is everything alright?” The other man asked sincerely. Dean just sighed.

“Yeah. Just going to miss this place, you know?” He smiled sadly.

“Oh, are…are you not going to be teaching anymore?” Cas tilted his head in confusion, looking way more adorable than a man his age should be able to.

“Yeah man, its my last day. I was only student teaching for the semester. Now that its over, I don’t need to anymore. I’ll be able to get my teaching certificate soon and have to start applying around. It’s possible ya know, I could end up back here, but… no guarantees.” He shrugged sadly, knowing this was the last conversation he’d have with the older man.

“Oh, that’s…that’s too bad. I’m sorry to hear that.” Dean was surprised to see that Cas actually did seem genuinely sorry too, and was that disappointment in his voice? No, Dean had to be reading that wrong. He was probably just projecting his own feelings onto the older man. There was no way he was actually sad about Dean leaving. He wasn’t crushing on Dean like Dean was to him, no matter how much Dean wished he was.

“Yeah, thanks Cas.” He just smiled sadly. “It was nice talking to you every afternoon.”

“You as well Dean. I’m sure you will be greatly missed.” _Yeah, but not by you_ , Dean wanted to say, but instead he just wished Cas a good afternoon and they said goodbye and that was it. No big to-do, just Bye have a good day. All of that pining and it was all just over.

His grumpy mood carried him home and he stomped his way up the stairs to his room before he slammed his door behind him and fell on his bed miserably. He decided it was a good time for a pity party, so he pulled out his phone and scrolled to his playlist of Led Zeppelin songs he liked to listen to when he felt like crap. He let the music wash over him as he thought of the blue eyes, he would no longer see every day. He had no idea how much time had passed when he heard a knock at his door.

“Come in.” He yelled, voice slightly muffled in the sheets, but it must have been clear enough because his door opened and he heard feet shuffling before the door closed again.

“Oh man, I figured you were in a bad mood, but damn! You looked like someone died or something.” His brother’s annoying voice reached his ears. He just harrumphed into the mattress, not bothering with a real reply. He hoped his brother would get the hint that he just wanted to be left alone; spoiler alert, he didn’t. Instead Dean felt the mattress dip as his brother’s lanky frame sat next to him where he still lay face down. “Come on man. Talk to me.”

“I don’t wanna talk about it.” He whined petulantly, not caring if he sounded like a child right now. He was sad, _alright_?

“Come on Deany, you can tawk to your wittwe brother.” Sam baby talked, annoying Dean even further. Sam then thought it was a good idea to repeatedly poke Dean in the side while chanting “Talk, talk, talk.” And Dean had finally had enough.

“Fine! Today was the last day of class and I’m not gonna get to see the Dad I’ve been crushing anymore!” He snapped, fed up with his brother’s antics. It was only after the words came out of his mouth, that he realized what he just did. He just fucking came out to his brother in a fit of anger. Definitely not the way he ever planned to tell him. Fuck.

“Shit. Shit shit shit…” He mumbled to himself, face red. He frantically tried to figure out how to fix this, but came up blank. He must have been silent to long because Sam just cleared his throat, causing Dean to finally look up and see the smirk on his little brother’s face.

“You were crushing on one of the Dad’s of your students?” Sam chuckled, making Deans face heat even more in embarrassment. “Was he a DILF?” he said chuckling even more. Dean was about to tell him to go fuck himself when he realized something. Sam didn’t seem surprised he was gay.

“Wait, you’re not freaking out over this?” He asked confused.

“About you crushing on a Dad? No, its pretty funny though.” His brother snickered.

“No, about me being gay.” He clarified, eyes rolling in annoyance.

“Dude. I’ve figured you were gay for years.” Sam scoffed. “You have always had male celebrity crushes. It wasn’t that hard to figure out.

“Huh….” He muttered at that revelation. He had been so worried about coming out and Sam had known all this time? “And you…you, d-don’t care that I’m gay?” His squeaked uncertainly, praying that Sam really didn’t care.

“’Course not dude. You’re my brother. I love you. I couldn’t care less who you’re attracted to.” Sam shrugged, a softer smile on his face now. Dean felt his eyes begin to well up, and tried to hold them back.

“T-thanks man.” He whispered, before Sam pulled him into a hug. “Just d-don’t tell anyone else, please.” He begged as he hugged his brother back.

“Your secret is safe with me man.” He promised. “But I really don’t think mom and dad would care if you told them.”

“Yeah, that’s what Charlie said. I-I’m just not, uh… ready yet.” He confided in his brother, feeling lighter than he had felt only minutes before. A third person knew his secret and the world didn’t end. Maybe he’d eventually feel brave enough to tell his parent’s, but for now, it felt good that his brother knew and still looked up to him. He’d worry about the rest of the world later.


	7. Chapter 7

“Come on, Red…Do we _really_ have to be here?” Dean whined as they entered Club 608, a gay bar close to where they both lived. The atmosphere was pretty laid back, and you really wouldn’t even know it was a gay bar if it wasn’t for the LQBTQ+ flags lining the walls. There was a long bar on one wall, a small dance floor, and a pool table in the back. It wasn’t too crowded tonight, just enough people that no one would really stand out.

Charlie had basically dragged Dean here, after two weeks of annoying him relentlessly, before he finally caved and agreed to come. He didn’t really want to, but Charlie insisted he needed to ‘put him self out there’ and ‘cheer the fuck up’-her words, not his. It was February, and it had been two months since he had finished teaching; two long months of Dean being a ‘miserable sack of shit’-again, Charlie’s words, not his. His last semester of school had started last month and he really tried to focus on his last few classes he needed before he could get his degree and start teaching for real, but his thoughts were consumed by the blue-eyed man he hadn’t seen since December.

He figured he should have been over Castiel by now. He hadn’t seen the man in two months, and they had only really been acquaintances anyway; They hadn’t even been true friends. They had only had very brief conversations every afternoon, but Dean missed those conversations terribly. He had apparently been having a pity party too long, because Charlie finally sat him down and told him he needed to get over it and move on. Hence, her brilliant idea of dragging him to this bar. She insisted he needed to try putting himself out there and get himself a boyfriend so he could stop pining over his crush.

“Yes, Dean, we really have to be here. If I have to hear you bitching about missing your crush one more time, I will go insane.” She grabbed him by the shoulders to make him look at her, eyes wide and serious. “I love you; I really do. But you need to get over him. Hit on some guys your own age and maybe get laid.”

“Fine. Fine…. I’ll try to meet someone.” He conceded, shoulders slumping in defeat.

He had no real intention of meeting someone tonight, he just went along to appease his friend. He figured he could have a couple of beers, try to talk to a few cute guys, and maybe play some pool, before begging off to go home, claiming he was tired.

*************

Cas just sighed as he followed his brother into the little bar they had arrived at. Bianca was having a sleepover with her friend Callie, who lived a couple of houses down from them. Gabe had decided that they should go out and take advantage of Cas’ childfree night. He had conveniently neglected to mention that they were going to a gay bar though. Apparently, Gabriel though he needed to ‘get laid’. Cas had really just wanted a quiet night in, relaxing with a glass of wine and a good book, but his brother wouldn’t hear it and dragged him out instead. Cas still doesn’t remember agreeing, but somehow, he found himself sitting at a high top in the corner of the room, as Gabe pointed out different guys he thought were perfect for Cas to hook up with.

“What about that one over there?” Gabe suggested, and Cas turned around to look.

“Absolutely not, Gabe!” He hissed after seeing the person in question; An extremely muscular man that looked like he lived at the gym. He was literally the opposite of what Cas was looking for. He didn’t have the slim body that Cas fantasized about every night, nor the freckles that haunted his waking hours. Essentially, he wasn’t _Dean_ ; The young man whom Cas still nursed a massive crush on. The young man Cas had not seen for two months now, but who still featured in every one of Cas’ nighttime fantasies. It was ridiculous how much he was still hung on Dean, but no matter how much he tried not to, he couldn’t help but pine after the other man.

“Well then pick someone else Cassie! I’ve tried to help, but you haven’t liked a single one I chose!” Gabriel complained loudly.

“I didn’t ask for your help. I have no desire to ‘hook up’ with someone right now. You dragged me here against my will.” Cas seethed through gritted teeth, annoyed at his pain in the ass brother. “I’m going to get another drink.” He stormed off towards the bar, completely done with the whole thing.

He waved the bartender down, and ordered a scotch before leaning against the bar and rubbing a hand down his face. The bartender reappeared less than a minute later, drink in hand.

“Thank you.” He politely smiled as he placed a tip down.

“ _Cas_?” He heard a familiar voice behind him, causing him to turn and stare into the face of the man he thought he’d never see again.

“Dean? W-what are you doing here?” He stammered in shock. Dean was here. Dean was _here!_ Dean was standing in front of him at a _gay bar_ , looking just about as shocked as Cas was.

“I-uh…I could ask you the same question.” Dean countered; his eyes still wide in surprise.

“My, uh…my brother dragged me here. He is attempting to be my- um…what’s the word…. Oh, yes. he’s attempting to be my ‘wingman’” He air quoted in explanation.

Deans’ brows pinched into a confused expression “You, uh…you know this is a _gay_ bar, right?”

“Of course, I do. That is typically where a gay man would go to ‘hook up’, is it not? ” Cas’s face mirrored Dean’s confusion now.

“Oh….” Dean’s browns fled to his hairline at Cas’ words. “I, uh, I didn’t know you were gay.”

“Well, I am, 100 percent so.” Cas shrugged. He was used to people who knew he had a daughter, assuming he was straight. It didn’t really surprise him that Dean apparently had been under that false impression as well. “What are you doing here?” He asked curiously, hope beginning to bloom in his chest knowing that the younger man was most likely gay as well. Something he hadn’t considered before tonight. He had been positive that Dean couldn’t possibly swing his way.

“Same as you I guess” He chuckled lightly, hand going to the back of his neck in what Cas was coming to realize was a nervous gesture. “Charlie-my friend from 7-eleven? She dragged me here as my wingman too. Said I needed to get over….” He stopped himself, blush forming on his freckled cheeks. “Uh, that I needed to get out there and find a boyfriend, heh…”

“I thought you were straight…” The older man blurted out, first thing that came to his mind.

“Guess we both thought wrong huh?” Dean joked, and Cas joined in as they both just stood there awkwardly, not knowing what else to say. Luckily, they were saved by Charlie coming back from the bathroom.

“Cas! Hey its so good to see you! You haven’t been in the store in forever!” The red head squealed excitedly before punching Cas’ arm playfully.

“I’m sorry Charlie. I’ve been so busy with work; I haven’t had the occasion to stop by.” He apologized, smiling at the bubbly woman. He really needed to stop in at the convenience store more; She always made Cas smile.

The three of them made polite, though stilted, conversation, before Dean decided he was tired and wanted to head home. Cas wished them both a good night, before making his way back to his brother. As he reached their table, a hand grabbed his bicep, turning him around, where Charlie stood before him, face set in determination.

“Listen, Cas. Dean will probably kill me if he finds out I’m doing this, but here, take his number.” She thrust a piece of paper into his hand. “He has an epic crush on you. Dude’s been miserably pining over you since December, and if I have to listen to him brood anymore, I’m gonna kill him. Call him please!” She pleaded before running back out the door, leaving Cas standing there gaping like a fish.

“What was that all about?” Gabriel asked, pulling a lollipop out of his pocket to suck on.

“I’m, uh n-not sure.” He stammered, mind still racing at what just happened. “I think my options just opened up though.”


	8. Chapter 8

Dean walked out of the bar with Charlie, mind still reeling about the fact that Cas was actually gay, before Charlie stopped and told him she forgot her phone at the bar. She ran back in to get it while he waited outside for her. She was only gone a few minutes before she came back out, and they walked the mile back to their street. He was quiet, lost in his thoughts when Charlie nudged his side.

“Soooooo….” she trailed off as she wiggled her eyebrows teasingly.

“Ugh Charlie, don’t start.” He whined. He was too tired to deal with her pestering right now.

“Oh, Come on! You just found out the dude you’ve been pining over is gay too! Aren’t you happy? Excited? Over the moon?” She ribbed. “You should have a smile on your face right now!”

“Happy now?” He pasted a forced smile on his face, hoping to shut her up as he continued on ahead, walking faster. The quicker he got home, the quicker he could end this conversation and be alone with his thoughts. He still needed to process everything that happened tonight.

Charlie caught up to him, and grabbed his arm to stop him from walking away. “Sorry, I won’t tease you anymore tonight.” The teasing tone was gone from her voice now. “I’m just excited for you. You’ve been miserable for two months over that man. You thought he was straight and that you’d never see him again and _both_ of those were proved wrong tonight. You have a chance now Dean. We could come back here a few times and maybe you’ll run into him again.” She offered, and Dean felt a tendril of hope inside at the thought that maybe that could happen. He told himself he was being foolish though.

“Just because Cas is actually gay doesn’t mean I have any more of a chance _now_ , than when I thought he was straight. He’s much older than me _Charles_ , and for all we know, I’m probably not even close to his type. Dude probably likes fit, muscular guys who could bench press like, a thousand pounds or something. What would he want a twink like me for?” He challenged, self-deprecation clear in his voice, and his shoulders slumped in sorrow, before he felt a sharp sting on his bicep.

“Fuck, Charlie…Ouch! Geez! What the hell was that for?” He complained, as he rubbed the sore spot on his arm where his best friend had punched him. She may be tiny, but _man_ , could she pack a punch.

“Don’t talk about my best friend like that.” A firm glare on was on her face, before it softened slightly to go on. “You’re an adult Dean, you aren’t some scrawny kid. And Cas would be lucky to date you. Just…think positively for a change.” His mouth turned up slightly at the corners at her words, and he pulled her into a hug, kissing the side of her head as he did.

“Thanks Red. You’re the best.” He told her as they parted.

“And don’t you forget it!” They both laughed.

Dean had seen her safely inside her own house before he walked the two blocks over to his own home. They had grown up on this street together, since elementary school actually, and had been best friends the whole time. Charlie basically took him hostage the first day of kindergarten, declaring them best friends, and Dean just went along with it. When they realized they lived so close, they had both been ecstatic little kids and sleepovers became a regular thing. It wasn’t till they became teenagers that those had dwindled down. _Apparently_ , it wasn’t _appropriate_ for a 13-year-old girl, and a 13-year-old boy to sleep in the same room together anymore. Pft, its not like they were going to do anything; They were both _gay_ after all. But neither set of parents had known that at the time. Hell, Dean’s parents _still_ didn’t know. Charlie’s did though. She had come out to them in high school and luckily, they had been supportive. Dean was happy it had gone well for her. He still wasn’t so sure how it would go for himself, and he knew time was drawing nearer for him to come out to his parents. He didn’t want to be one of those middle-aged men who were still in the closet. Maybe once he had a boyfriend- an actual _reason_ to come out- he would tell them. Yeah, that was a good idea. Its not like it mattered much now since he wasn’t dating.

He slept that night peacefully, and woke up the next day refreshed. It was Saturday so he didn’t have any real plans besides vegging out and watching Netflix. He was a couple of hours into a binge when his phone began to ring. He looked at the caller ID, and didn’t recognize the number, but it was local so he answered.

“Hello?”

“Is this Dean? “The man asked. His voice sounded familiar, but it was always hard to tell through phones.

“Yup, this is he.” He was curious who could be calling him.

“Oh good, Hello Dean. This is Castiel.”

“Cas?” His voice faltered “Uh, how- how did you um, get my number?” He chewed on his bottom lip.

“Uh, your friend-Charlie, she uh…she gave it to me last night.” Dean was going to kill her. He was going to get his dad’s shotgun, shoot her, and then chop her up into little tiny, itty bity pieces, before feeding her to the wild animals.

“Oh um…that’s cool.” He wanted to kick himself for the lame reply. Why was he always awkward with Cas? Ugh?

“Yes, well…I was wondering- that is- I uh, wanted to know if, maybe, you would like to go out. To uh, dinner. Go out to dinner. With me. “Cas stammered out, as awkwardly as Dean felt, and he could just picture the adorable blush the older man must be sporting right now. Then his words finally registered in Dean’s slow brain.

“Wait…what?” He blurted out dumbly, the words not making sense to him. There was no way he heard that right.

“You don’t um, have to feel…. obligated, I just…. You know what? This was a bad idea. I’m just going to hang up n….” Cas stuttered before Dean interrupted his babbling.

“Hold up, just…hold up, Give me a sec, alright? You don’t need to hang up Cas. I uh…I just wanted to make sure I heard you right.” He gathered his courage before he continued “Are you, um, asking me on like, a…Date?” The back of his neck felt warm, and he fiddled with the loose string on his pants as he awaited a reply, hoping against hope that he hadn’t misinterpreted the question.

“Y-yes. Yes, I am. If, that’s…um…. something that would, interest you?” Cas affirmed, voice lifting up in question at the end.

Dean was gob smacked, and gaped like a fish before he was finally able to croak out a response. “Yeah…definitely, um, interested.”

“Oh, Okay good.” Dean heard what sounded like relief “How is next Friday night? I could pick you up at 7 and we could go to dinner?” The other man asked more confidently than before, uncertainty gone from his voice.

“7 is good.” Was all Dean could manage, still in disbelief at the what was happening; His brain shorted out trying to wrap his head around it all.

“Ok, great. I will text you later this week with the details. I look forward to our date.”

They ended the call with the normal pleasantries, and Dean immediately called his best friend.

“Hey D- “She started before he rudely interrupted her.

“He asked me out!” He shouted, as he paced in his room, hands reaching up to tug at his hair.

“What? Who? What are you talking about?”

“Cas, Charlie! Cas! Cas asked me out!” Manic chuckles escaped his lips; his voice in hysterics as he tugged the hair on his head.

“He actually did it?!” She squealed excitedly, reminding Dean how Cas had gotten his number in the first place.

“What in the _Hell_ , possessed you to give him my number?” He demanded angrily at his best friend.

“Don’t even try to pretend like you are angry with me, Winchester.” She scoffed. “You should be thanking me. I did what you didn’t have the vagina to. Now you have a date with Mr. Dreamboat.” Her voice was smug, and he wanted to argue, just on principle, but he knew she had a point. He felt the fight leave his body as his hand fell down from where it was tugging at his-now fucked up-hair.

“Ugh, fine. Thank you.” He grumbled reluctantly. “The date is on Friday and I’m making you help me get ready for it. I haven’t the first clue how to dress for a date.”

He could hear the glee in her voice when she responded “Yes! We’re going shopping bitches! Oh, montage!”


	9. Chapter 9

**Summary for the Chapter:**

> They go on their date.

Charlie had dragged Dean to the mall on Sunday to help him pick out an outfit for his upcoming date. He figured it would be a quick trip, maybe try on a few clothes, have some lunch, and then go home to watch Dr. Sexy. He hadn’t known that Charlie wasn’t kidding with her ‘montage’ comment. She made him try on outfit after outfit, and by the end of it, he had felt like a model after a long day on the runway. He had been so exhausted when they got home that he fell into bed, and didn’t even get around to watching the new episode of his favorite show until the next day after classes.

The week went by, both too slowly, and too fast for Dean. Between classes, and picking up a few hours at his Uncle Bobby’s garage, he stayed busy; counting down the days until Friday and the Big Date. He mood constantly shifted between nervous and excited, rarely sticking to one before flipping to the other. The funny part is that the reasons he was excited wer the same reasons he was nervous.

Its his first date, so obviously he’s excited to finally be going out on a date with another guy, especially since he is 22, and most people his age have been dating for years at this point. But its also his _first date_! He has zero experience in this area and he’s scared he is going to fuck it up somehow. _What if he squirted lemon into his eye while trying to squeeze it into his iced tea? Or what if they went to hug goodbye and he farted? Or what if they were leaning in for their first kiss and he got sick and puked all over the place?_ Damn, he really needed to lay off the Buzzfeed articles before he talked himself into a panic attack.

Also, this was a date with _Cas_! Cas; the man Dean had pined over for 7 months now, ever since July and that Carnival. He was going on a date with the man of his dreams- _dirty_ and otherwise. He’d daydreamed about this for so long, it almost didn’t feel real that it was about to be a reality. But he was also incredibly nervous. They had already had their fair share of awkward moments, so it was a real possibility that the date would end up being incredibly awkward too, which would royally _suck._

So, yeah. To say Dean was on edge most of the week was an understatement. He stood in front of his bedroom mirror, as he buttoned up his shirt and tried to psyche himself up. The outfit Charlie had helped him pick out looked classy, without looking too dressed up. He had on a dark pair of black-fitted jeans, that hugged his body in all of the right places. It accentuated his “bubble-butt”- as Charlie had referred to it-, and hugged his bowed-legs snugly. He paired it with an emerald button-up, that Charlie had told him complimented his green eyes. He styled his hair with a bit of gel to complete the look. Cas would be coming any minute and Dean was trying not to freak out and sweat through his clothes.

He made his way down the stairs to wait outside for his Date. He didn’t want Cas coming to the door and risk his parents finding out he was going on a date with a guy. He had just told them a friend was picking him up to go out to a club so they didn’t question his choice of outfit.

He stood on his front porch until he saw an old Lincoln Continental pull up to the front of his house, and who he assumed was Cas in the driver’s seat. He made his way to the vehicle and climbed in the passenger seat.

“Hello Dean.” Cas smiled shyly as Dean buckled himself in.

“Hey Cas.” The butterflies in his stomach felt like they were doing the quick step. “So, uh…where are we going tonight?”

“I thought we would go to Don Ricardo’s on Main Street, if that’s ok with you?”

“You know, I’ve never actually been there, but I’ve heard they have really good food. And apparently their peach margaritas are amazing.” Dean offered in response.

“They are. I’ve been there a few times with old colleagues of mine. The food is very delicious.” Cas assured as he pulled away from the curb. They made small talk on the short drive to the restaurant. Dean found out that Cas was a free-lance computer programmer who mainly designed websites for clients right now. Dean, in turn, told Cas that he worked part-time at his uncle’s garage while he attended school.

When they reached the restaurant, they were seated immediately, lucking out that there was no wait. The waiter took their drink order and both men glanced at their menus in silence. Once they ordered their food, and the waiter took their menus away, Cas glanced up at Dean.

“I’m very glad you said yes to this date.” The older man smiled sincerely.

“I’m very glad you asked me on this date Cas. I uh…I’ve been, um… kinda crushing on you for…uh… awhile now.” He confessed, fiddling with his fingers nervously, where they rested in his lap.

“Yes, Charlie might have mentioned that.” Cas’ grin turned sly as he revealed that bit of information, making Dean groan as the tips of his ears burned.

“Ugh, I’m going to kill her.” He muttered quietly, making the other man chuckle.

“Don’t. I’m glad she did. I will admit I was very surprised though, when she came back in the bar to give me your number last week and told me. I had no idea you returned my attraction to you.” Dean didn’t think his blush could get any worse, but he apparently had been wrong. Just hearing Cas say he was attracted to him so matter-of-fact had his heart racing, and his palms sweating. He took a big gulp of his drink- _damn the peach margaritas really_ were _good_ -before offering his own shy smile.

“Same man. I still can’t believe you’re gay too. I uh, I really thought you were straight, cuz of Bianca and all…” He trailed off, not knowing if he should ask how she came to be. Luckily, Cas took the decision out of his hands.

“Ah, yes. I get questioned a lot about how I have a daughter, being a single gay man and all. Long story short, I was drunk at a college party and hooked up with my friend Meg. It was-awkward to say the least. It also cemented the fact that I am definitely gay.” Cas chuckled lightly before continuing. “Two months after that, Meg came to me telling me she was pregnant and wanted to give the baby up for adoption. I…” Cas closed his eyes tight, looking pained. “I couldn’t bear the thought of giving away my own child. I begged Meg to give me full custody. So, when Bianca was born, Meg signed over all rights to me and pretty much disappeared. So, uh…that’s, that’s the gist of it.” He shrugged, before taking a sip of his own drink.

“Wow, so you were, uh…pretty young then when Bianca was born?”

“Yes, I was 22.” He nodded.

“Damn…” Dean blew out a breath. Cas had been so young and had to raise a baby without a partner. “That had to be hard.”

“Heh, you have no idea. If it hadn’t been for my brother Gabriel, I don’t know what I would have done.”

“What about your parents? They didn’t help?” He asked curiously. A dark look passed over Cas’ face and he grimaced.

“No. They uh… they threw me out of the house and disowned me, when they found out I had ‘knocked up’ a girl I wasn’t even dating.” Those damn air quotes made the butterflies reappear inside Dean. The man was way too adorable for his age. “It was bad enough that I was gay, but having a child out of wedlock too? That was too much for them. Gabriel took me in and helped me with Bee. I was fresh out of college with no money to my name and no job yet. I would have been on the streets if he hadn’t been there for me.”

“Wow, man. I’m uh… I’m glad you have such a good brother then.” Dean offered, awed by how much Cas had gone through. He couldn’t imagine his parent’s throwing him out of the house.

“He can be a real pain in the ass sometimes, like last Friday…” Cas chuckled fondly “But I owe him everything. He was there for me when I had no one. He still has my back when I need him. I wouldn’t be where I am without him.”

“Yeah, I hear ya. My brother bugs the crap out of me sometimes too, but he has my back. I uh… I actually just came out to him a couple of months ago and he real cool about it. Actually, it was kina funny, he didn’t care that I was gay, he just teased me about having a crush on one of my student’s parents and asked if you were a DILF…” Dean’s babbling cut off and his eyes shut tight as he prayed a hole would appear below him and suck him right in. He felt his face get hot again and it was the deep gravely laugh that made him open his eyes and look up at Cas. The other man had his head back in laughter before he looked in Dean’s eyes; lips turned into smirk.

“Well…am I?” Cas quirked an teasing eyebrow in question.

“Could we pretend I never said that last part out loud?” Dean pleaded, wishing he could erase the last two minutes of his life.

“Hm…” Cas pretended to ponder that before shaking his head teasingly “Not a chance. Sooo….am I a DILF Dean?” He asked again, shit-eating grin on his face.

“Yeah, alright? Yeah you’re a DILF Cas.” He grudgingly admitted, face about the shade of a tomato at this point. And the conversation had been going _so well_ too.

“Good to know.” Cas smiled smugly.

“Ok, now that I’ve _completely_ embarrassed myself, lets talk about something else.” Dean suggested. “So, if you were 22 when Bianca was born, that’d make you what, 30 now?” He pondered out loud.

“Yes, I turned 30 back in December. And you’re how old? I’m assuming at least 21 since they IDed you for that margarita you are drinking” Cas questioned in response.

“Twenty-three actually. My birthday was last month.” Dean told the other man. “Is, uh…is that okay?” He asked timidly, still unsure whether his age would be a deal breaker or not for the older man. He got an eyeroll in response.

“Of course not, Dean.” He scoffed. “I figured you were around that age since you are in college. Your age is not a problem for me” Cas assured before his smile faltered. “Is uh, is my age a problem for you?”

“No, no. No, absolutely not.” Dean was quick to assure the other man, a smile returning to Cas’ face.

“Ok good. So that’s settled then. Age difference is not a problem for either of us. That’s one of the elephants in the room taken care of at least.”

“One of? There another elephant?” Dean asked confused.

“Well, I’m uh…assuming its not a problem since you already know about it and agreed to this date….” Cas ran his fingers through his hair in what looked like a nervous reflex. Well at least now his perpetual face-fucked look made sense. “I have a daughter-which you obviously know since you were her teacher- but I just want to make sure you’re aware of what that entails if we, um…if we decide to continue dating.” Cas explained, uncertainty clear in his voice.

Ah, so Cas was worried about how Dean would handle dating someone with a kid.

“Don’t worry Cas. I know your daughter is the most important person in your life and that she will always come first.” He assured him. “I love kids, which is why I’m becoming a teacher first of all, and I’m fully aware that you are a package deal.”

“And you’re okay with that? Because its fine if you aren’t Dean. I’ve dated people that were cool at first with me having a kid, but then once the reality of what that meant set in, they bailed. I-I know this is only a first date and everything, but…. I’d rather know now whether or not you see this going anywhere, rather than a few months down the road.” Dean really wanted to hug the other man, seeing the resigned look in his face. He had obviously been hurt before, to be giving Dean this speech right now.

“Cas, look. I can’t promise right now that this will last, obviously. But I know that you being a parent is not something that is gonna play into that at all. I like you, a lot. And I’d like to see where this goes, if you do too.” And he did. He really liked Cas and would love to go on more dates with him. He knew going into this that Bianca was part of the deal. Hell, he already knew the little girl well and he liked her too.

He was rewarded with a gummy smile from the other man. “That makes me feel a lot better.” Cas sighed in relief just as the waiter delivered their meals.

They both ate in mostly silence, only offering comments on how well the food was, but Dean was pleased to find that the silence wasn’t awkward. It was rather nice to just enjoy a meal in the other man’s company, sharing small smiles between bites. Before long the food was gone and the check came. They argued over who should pay-Cas insisted since he invited Dean that he be the one to pay- and Dean finally relented after Cas agreed he could pay for a future date.

They drove back to Dean’s house and parked in front, Dean glad to see that the lights were off and his parents most likely in bed already.

“I had a great time tonight Dean.” Cas said as he turned in his seat to look Dean in the eyes.

“Me too Cas.” Dean smiled shyly.

“I was wondering…. Would you want to come over to my place for dinner sometime next week? Bianca will be there so it won’t be a proper date, but I thought it might be good for her to start getting used to seeing you again, outside of school this time, if we are doing this. We could just tell her we are friends for now.” Dean’s insides lit up like a Christmas tree, and he knew his beaming smile probably looked a little too eager but he didn’t care.

“Yes. I-I’d love to come over for dinner Cas. I miss Bianca too.”

“Okay great. We can discuss details later this week.” Cas beamed in return. “Here, I’ll walk you to the door.” Cas unbuckled and turned to exit the car, making Dean freeze up in panic.

“Uh, th-that isn’t a good idea.” He stammered.

“Why not?” The other man’s hand dropped from where it was reaching for the door handle, and his head tilted in confusion.

“My uh…my parents don’t know I’m g-gay” He stammered, embarrassed to admit that. Cas would probably rethink the whole age difference thing now. 

“Oh, well I can see then why me walking you to the door and kissing you goodnight might not be a good idea then.”

“Youcankissmerighthere” He blurted out without thinking, so fast it came out as one big word. “I-I mean….” _Fuck._ Idiot. He was an idiot. Who the hell just blurts that out? He chastised himself, eyes cast down in embarrassment before he felt a finger tilt his chin up.

Cas was smiling fondly before he slowly leaned in. Dean’s eyes closed in instinct before he felt soft lips touch his own. _Holy crap!_ He was kissing _Cas_! He was _kissing_ Cas!

There were no fireworks, or sparks, or any of that stuff he read in the romance novels he would never admit out loud to reading. Instead, there was warmth and contentment rushing through his body as Cas brushed his hand up to cradle Dean’s jaw. Their lips fit together perfectly and Dean sighed as he sank into the kiss. It was over quick-too quick if you ask him- but Dean had never felt happier in his life. As far as first kisses go, he was pretty sure his was one of the best.

He was sure he had a dopey smile on his face when they slowly pulled apart. He felt his chest constrict as they stared into each other’s eyes, something profound passing between them. He felt the need to say something, anything to lighten the heaviness of the moment.

“That was…nice.” He wanted to kick himself for such a lame description of what they had just shared, but _sue him_ , he just had his first ever kiss and his brain wasn’t firing on all cylinders right now.

“Yes, it was.” Cas agreed, warm smile still on his face. “I look forward to next week Dean.”

“Yeah, Cas…me too.” He whispered shyly. “I, uh…better go before someone wonders why we’ve been sitting here so long.” He joked as he reached for the door handle. “Night Cas.”

“Good night Dean.”

He climbed out of the passenger seat and shut the car door behind him, before making his way up his front steps. He turned to look at Cas and gave a small wave as the other man drove off. He pulled his keys out of his pant’s pocket and unlocked his front door, making sure he was quiet as he let himself in and locked up behind him.

When he got to his room, he threw his jacket on his desk chair and stripped down to his boxers, before he slipped underneath the covers of his bed. He didn’t remember ever being this happy before in his life. He fell asleep that night with a smile on his face, as he thought about how their next date at Cas’ house would go.


	10. Chapter 10

Cas spent all day Wednesday fretting around his house cleaning. There wasn’t even much to really clean, since he was a normally a tidy person anyway, and Bianca was past the age where it constantly looked like a tornado blew through his house. But he needed everything to be perfect.

He and Dean had decided on tonight for the other man to come over for dinner, and Cas was a nervous wreck all day. He wanted- _no needed_ \- this to go smoothly. This was the first prospective relationship he had in years, and he didn’t want it to fail before it even started. He had already warned Bianca ahead of time to be on her best behavior. Not that he really had too much to worry about there; his daughter was a pretty well-behaved child after all. Sometimes, though, she had a habit of repeating inappropriate things at the worst times. Castiel still cringed when he thought about the couple of times she had done so at school in front of Dean. He had really tried to watch what he said around her after that.

Bianca had been very excited when he told her that Dean was coming over their house for dinner. She seemed to really like him, and that made some of the anxiousness over dating the other man dissipate. He hadn’t been kidding when he told Dean that it was difficult dating as a single parent; Many men had said adios after meeting Bianca, not because of anything she did, just because once the fact that he had a kid was right there in their face, they realized they wanted no part of it. He guessed many of them assumed that he was one of those dads who only had their kid on the weekends or something, rather than full-time like he did. He had a good feeling about this though. Dean and Bianca already knew each other, having spent six hours every weekday together for three and a half months. They also both seemed to like the other. Cas just hoped that would carry over into a more personal level outside of the classroom as well.

He was just placing the meatloaf into the oven when he heard the doorbell ring.

“Bianca! Mr. Winchester is here! Please come downstairs!” He yelled up to his daughter, as he made his way to the front door to greet the other man. Dean stood on the other side of his front door; a smile on his handsome face.

“Hey Cas.”

“Hello Dean. Please come in.” Cas smiled as he stepped aside and held the door open for the other man. Dean came inside and Cas shut the door behind him.

“Here, I brought a bottle of wine. I know how much you enjoy your grown-up drinks.” Dean teased, referencing one of those times Bianca embarrassed him.

“I’m never going to live that down, am I?” He groaned, making the younger man chuckle.

“Nope.” Dean replied cheekily, popping the last syllable of the word. “Hey, at least your daughter already knows never to drink and drive.” He winked, sending heat down the base of the older man’s spine. _Not the time for inappropriate thought!_ He internally chided himself before shaking his head.

“Like that saying goes, kids say the darndest things.” Cas sighed.

“Oh, I know. Trust me. You have no _idea_ the amount of times I had to turn my head so the kids wouldn’t see me laughing when I was in the classroom, heh.” Dean chuckled.

“If the other kids were anything like Bianca, I can only imagine what came out of their mouths.” Cas joked as they made their way into the house, Cas taking the wine from Dean to put on the kitchen counter as they passed through into the living room. “Dinner will take about an hour to cook, so I figured we could sit and talk for a bit first, if that’s okay.”

“Sure, yeah. That’s fine Cas.” They both took seats on opposite ends of the couch and turned to face one another, just as Cas heard loud stomping down the stairs.

“Bianca, how many times have I told you not to run down the steps?” He scolded his daughter as she turned the corner into the room.

“Sorry Papa!” She apologized before turning her former teacher. “Hi Mr. Winchester!” She greeted excitedly.

“Hi Bianca. Please, call me Dean. I’m not your teacher anymore.” He told her kindly, causing her to wrinkle her nose.

“It’s weird to see you not at school Mr.-I mean- Dean.” She told him bluntly, pulling another chuckle out of the younger man.

“Well, its weird to see you out of school too Missy.” He stuck his tongue out at her childishly, making her giggle. It tugged at Castiel’s heart to see Dean interacting so playfully with his daughter. Before his thoughts could run away from him and start imagining an entire sappy future with the three of them together, he cleared his throat.

“How about we put on some music?” He suggested, making Bianca’s face light up.

“Taylor Swift, _please_ papa can we listen to Taylor swift? Please please please!” She begged. Cas just sighed.

“That’s up to Dean, sweetheart. He is our guest, so I think he should be the one to pick. Don’t you?” He asked her with his best Dad voice, knowing she knew her manners and how they treated guests. He was really banking on Dean wanting to listen to anything other than the incessant Pop music his daughter was so fond of. He could sing most of the uppity music in his sleep at this point.

His daughter pouted for a second before looking at the other man. “What do you wanna listen to?” She asked him.

“I think Taylor Swift sounds good.” Dean smiled at his daughter in agreement.

“Yes!” She shrieked, making Dean laugh.

Cas gasped in mock outrage. “Traitor!”

“Hey Bianca. You know what I think.” Dean smirked, a conspiring glint in his eyes.

“What?”

“I think the players gonna play, play, play, play, play. And the _haters_ gonna hate, hate, hate, hate, hate.” The younger man broke out in song, making sure to put emphasis on the “haters” part. Bianca giggled so hard at Dean’s antics, and Castiel just shook his head in resignment.

“I guess I’m outnumbered here.” He grumbled as his daughter yelled for Alexa to play Taylor Swift. He turned to look at Dean. “You were supposed to be on my side.” He whined.

“Hey man, you can’t go wrong with Swift.” He held his hands up in defense.

Music started playing from the speaker and both men watched Bianca dance around as she belted out the lyrics to the current song. They glanced over at each other and smiled at her enthusiasm.

“She’s adorable Cas.” Dean complimented, making Cas smile wider.

“I agree. At least most of the time.” Cas joked. They stared at each other, caught in each other’s eyes before they were interrupted by his daughter.

“How do you make the bad guys good for a weekend?” She asked curiously. Cas watched Dean’s eyes go wide before he threw his head back in roaring laughter, as his own face began to heat in mortification.

“Th-that’s…um…wha…why are you asking that?” He sputtered out.

“It’s in the song Papa.” She rolled her eyes “What does that mean? How do you make the bad guys good for a weekend though?” She questioned again. Cas could see Dean doubled over now, and Cas sent a glare his way before turning back to his daughter.

“You tell them to be nice because its not good to be bad.” He lied through his teeth, not even remotely ready to be discussing the actual meaning of those lyrics with his eight-year-old daughter.

“Oh, okay that makes sense.” She nodded before continuing to jump around to the music. Cas turned back to Dean who was wiping tears from his eyes still.

“Really Dean?” He sent an unimpressed look the other man’s way.

“Dude…. I-I’m sorry…. b-but that…was hilarious.” Dean wheezed out. Cas felt his own lip twitch at the younger man’s amusement.

“Yeah, well, thanks for your help.” Cas retorted; sarcasm clear in his voice.

Bianca danced to a few more songs, as the two men made idle chatter, until the oven timer went off. They made their way into the kitchen and Cas served them each a plate of food once they were all sitting around the table. They ate in mostly silence, enjoying the delicious meal Cas had made; Dean complimenting him on his cooking skills and Cas blushing at the praise. They were almost finished eating when Bianca piped in again.

“Are you gay like Papa?” She asked Dean, and Cas watched a small blush appear on the younger man’s cheeks.

“Uh…yeah. Yeah I’m gay like your Dad.” He told her honestly.

“Cool” she replied before eating another bite of her food. Cas smiled kindly at the other man, knowing he was still in the process of coming out to people. Dean probably shouldn’t have chosen that moment to take a sip of his water.

“Does that mean you guys are boyfriends?” The curious little girl questioned, face a picture of innocence. Dean spit out his mouthful of water all over the plate in front of him, and Cas froze, not sure how to answer that question.

“I…uh…well…we, um…” He stammered, looking up at the other man for help but seeing Dean’s shocked face was no better than his. “We…we are not boyfriends yet, Bee. We um, we have gone on a date though. So, I guess, I guess you can say we are dating?” He directed the statement as a question and saw Dean nod in agreement. He felt himself untense a bit that at least they seemed to be on the same page then.

“Hm.” She just hummed in response and kept eating as if she didn’t just make the entire meal awkward. Luckily, she finished soon after and Cas excused himself to go put her to bed, telling Dean he could wait in the Livingroom for him to return. When she had brushed her teeth and changed into her pajamas, he tucked her in and read her a story before kissing her goodnight and heading back out to Dean. He found the other man sitting on the couch, and he sat next to him, sighing as he relaxed into the soft cushions.

“Thank god she went right to sleep.” He exclaimed tiredly. “I don’t have to worry about what could come out of her mouth next now.”

“Yeah, that was…that was awkward.” Dean chuckled. “She really keeps you on your toes huh?”

“You have _no_ idea.” Cas muttered. “Talk about putting us on the spot.” He hmphed.

“Eh, what can you do man? Kids will be kids.” Dean shrugged. “I’ve had a good night so far.”

“Yeah?” Cas asked shyly.

“Mhmm. You know what would make it better though?” Dean smirked.

“What?” Cas asked curiously. Dean didn’t answer with words though; he gripped the front of Cas’ shirt and pulled him into a gentle kiss that had the older man’s nerves lighting up. He reached his hand up to Dean’s face and tilted his head to deepen the kiss. His tongue slipped out to probe at the younger man’s lips and Dean opened up for him; their tongues twirling together in a delicious dance.

The kiss became heated and he felt the younger man groan into his mouth in pleasure. Cas’ cock was hard in his jeans, pushing painfully at his zipper. He reached his other hand up the younger man’s thigh until he felt the hard outline of Dean’s cock as well and he pushed his palm down, stroking it through the other man’s jeans. He had expected the moan that came out of the younger man’s lips. What he didn’t expect however, was for Dean to also freeze and push Cas away roughly, as he jumped off of the couch.

“Dean?” Cas breathed, confusion and worry overshadowing the arousal he had been feeling.

“Sorry, I uh, I forgot I need to…get home early tonight. I-I…uh, I gotta go.” Dean stammered out, a fierce blush blooming on his freckled cheeks. Before Cas could wrap his head around what was happening, Dean had rushed out the front door, leaving Cas confused and momentarily stunned. When his brain finally got with the program, he jumped to his feet and ran out the front door just in time to see the gorgeous black muscle car fleeing down his street. He pulled out his phone and tried to call Dean, but it went right to voicemail.

Cas was so perplexed at what had just happened. He though everything had been going so well. He didn’t know why Dean had acted weird all of a sudden. Had Cas pushed too far? Why didn’t Dean say anything? He tried to call Dean a few more times that night, up until he went to bed himself, but every time he did, the call went straight to voicemail. He left a message asking Dean to please call him back. But as he lay in bed, he had a sinking feeling that his call would not be returned.


	11. Chapter 11

As Dean pulled away from the curb after fleeing from Cas’ house in a panic, his emotions were all over the place. Panic, fear, mortification, disappointment; you name it, he was feeling it. Things had been going so well too, he thought bitterly, before everything came crashing down because of his own inexperience. The kiss had been good, great even. And the bit of making out on the couch had been awesome at first, until Dean had to go and ruin it all. The second Cas touched Dean’s dick through his jeans, he had come in his underwear like the virgin he was. He did the only thing he could, and fled before Cas could realize what happened. It was bad enough that Dean knew what a loser he really was; he didn’t need Cas knowing it too.

His cell phone rang a few times-Cas’ name on the caller ID- but he sent each call to voicemail, not wanting to have to deal with it at the moment. Hell, he never wanted to deal with it. He would never be able to look Cas in the face and explain what happened without feeling like the idiot he was. Embarrassment and shame rolled off him in waves the entire drive back to his place.

Thankfully, his parents were out when he got home and he was able to slink up to his room without having to try to have a conversation with anyone first. Anyone would be able to see how upset he was, and he didn’t want to have to explain himself. He needed time to brood with his own thoughts before he had to interact with anyone like a normal person. He needed to lick his wounds in private, and try to forget about the other man. It’s not like they could continue to date. Dean would have to explain what happened first of all, and he knew once he did, that Cas wouldn’t want him anymore. Why would an experienced 30-year-old man want an inexperienced Virgin like Dean? Cas would probably be nice about it too, letting him down gently, but Dean wouldn’t be able to bare the rejection, regardless of how kind the older man was. No, it would be better if he just ignored any calls from Cas from now on. The other man would get the message eventually and they could move on. It hurt, but it would only hurt worse when he saw the look in Cas’ eyes when he found out what an embarrassment Dean was. Those thoughts consumed him as he finally fell into a restless sleep that night.

His mood didn’t fare any better the next day either, as he worked a shift in Bobb’s garage. The old man called him an ‘idjit’ a few times and told him ‘get his head out of his ass and get to work’ when he became distracted by his own brooding, and bumped his head on the undercarriage of the car he was changing the oil on.

Charlie noticed his bad mood as well, when they met for drinks that night. He tried to hide his feelings under a mask but she knew him too well.

“What’s got your panties in a bunch?” She prodded when they had sat in their usual booth.

“Nothing.” He lied.

“Liar. Come on Dean, what’s got you all mopey.” She insisted.

“I don’t wanna talk about it.” He Grumbled.

“Well too bad, I’m your best friend and its my job to cheer you up. So….let’s hear it. Come on, what’s wrong.” She pestered until Dean finally had enough and walked out, leaving her sitting there stunned. Luckily, they had come separately so he only felt slightly guilty leaving her there since he wasn’t leaving her stranded. But he really had had enough. He didn’t want to talk about it and she wasn’t going to make him.

****************

It had been five days since Dean had run out of his house and Cas was miserable. He had given up leaving messages since the younger man never returned them. At this point, Cas was pretty positive that things were finished between the two of them, as far as dating was concerned. Dean obviously didn’t want to speak to him and Cas would have to accept that. But he was concerned. He just wanted to talk to Dean one more time, at least to make sure he was okay. Something had bothered him that night, or he wouldn’t have fled like that. He wanted to at least apologize for whatever he did that made Dean upset. He could accept that they wouldn’t go on any more dates-as much as that pained him- but he just wanted to make sure the other man was ok.

Finally, it hit him, how he could find out; Charlie. She had to know how Dean was doing. After getting Bianca off to school on Tuesday morning, he made the drive over to 7-Eleven, hoping the fiery red-head was working. When he walked in the store and saw her behind the counter, his shoulders sagged in relief, and he walked up to the counter. The look on her face though, had his body tensing.

“What did you do?” She demanded, glaring at him with such anger that he was taken aback. He had only ever seen her bubbly, and didn’t even know she was capable of such venom in her voice.

“W-what do you mean?” He stammered, and received an eye roll in response.

“With Dean. What did you do? He’s been brooding miserably for the last few days and he won’t talk to me. I figured it had to be something you did since he started acting like this right after your little date last Wednesday. So, I ask again, what did you do?” She crossed her arms over her chest and stared him down, waiting for an answer.

“I-I honestly don’t know Charlie.” He said truthfully as his shoulders slumped in defeat. “The date was going really well as far as I knew, but…he uh, he just jumped up out of nowhere and fled. I tried calling him. I left, heh, I left at least a dozen messages but he hasn’t called me back.” He explained.

Charlie at least stopped glaring at him after the explanation. “Hmm…” She pondered aloud, a thoughtful look on her face. “And, you’re sure nothing happened that would have made him run out of there?” She asked curiously.

“Well…” He thought back to the date, “We were on the couch after Bianca went to bed and we started…uh…making out, and it got a little um…heated…” He trailed off, blushing at telling the woman any intimate details. Luckily, he didn’t have to clarify what he meant because immediately she seemed to catch on.

“Ah, well that explains it.” She replied with a nod, making Cas tilt his head in confusion.

“What do you mean?” He asked her.

“I think I know now why he ran. It’s not really my place to tell but I’m going to have a few words with the knucklehead and convince him to call you.” She promised.

“I don’t want him to do anything he’s uncomfortable with Charlie.” He insisted. “I just want to make sure he’s okay. That’s actually the only reason I even came in here in the first place. I feel horrible that I might have done something to unintentionally upset him.”

“Listen, Dean…. well…Dean can be an idiot sometimes. I love him like a brother but sometimes I really want to hit him upside the head. Look, Cas, If Dean is still interested, would you be willing to give him a second chance? I know if you two sit and actually talk about what happened, you’d understand. But I don’t want to give him false hope, ya know?” She shrugged.

“I think so…yeah, if he wants to try again, id like that. Especially if what you say is true and that I’d understand why he ran like he did, once he explains myself.”

“Ok good. Give me a few days to work on him and just make sure you answer when he calls.” She made him promise before she let him leave. He was still confused when he made it back home, but he felt a little less hopeless than he had earlier.

**************

It had been a full week since he ran out of Cas’ house and Dean was moping in bed, when his bedroom door suddenly flung open. Charlie barged in and shut the door behind her before she plopped down on the bed next to him and leveled him with a stern look.

“I talked to Cas yesterday.” She began, and Dean tensed up at the mention of the older man’s name. “Yeah, I knew your mood had something to do with him, and between what he told me, and your reaction just now, I’m pretty sure I know what happened.”

“I still don’t want to talk about it, Red.” He mumbled before hiding his face in his pillow. He really hoped Charlie had not actually figured anything out because it was embarrassing enough to think of without someone else being privy to the real reason he left Cas’.

“Tough shit Dean. I’m sick of seeing you like this, when I know its your own doing. So, either you spill, or I’ll start saying why I think you ran out of Cas’ house last week.” Dean remined silent, voice decidedly not wanting to work at the moment, so Charlie sighed and continued. “I think you got scared. Cas told me you guys were making out and things got heated and that’s when you ran. I think your own insecurities of being inexperienced came into play and had you freaking out. Am I getting warm?” She nudged his side hard, making him roll over.

“Ugh.” He grunted in response, throwing an arm across his face in embarrassment at being found out. Charlie pulled the arm away and he looked up at her, and saw the sympathetic look on her face.

“You have no reason to be embarrassed Dean. There is nothing wrong with being a virgin, okay? Everyone was at one point.” She told him softly.

“I fucking came in my pants alright?” He yelled in frustration. “He touched me once and I shot off like a damn rocket. So yeah, I have a reason to be embarrassed.” He snapped, face blushing as he replayed what happened in his head. He was still so mortified about that night.

“So what? So, you did something a little embarrassing, big deal. Its not the end of the world. And its not a good enough reason to ghost Cas like that.” She argued.

“He’s better off without me anyway.” He muttered.

“Don’t be so melodramatic.” She rolled her eyes in annoyance. “I could clearly see how much he was hurt at you running out on him with no explanation. And he was really concerned that he did something to upset you. He deserves an explanation at the very least.” Charlie was right. Dean was an ass for making Cas think he did something wrong. “Plus, I really think after you explain what happened, he’d still be open to dating you.”

“Ugh. I doubt that. But I guess you’re right.” He conceded “I do owe him an explanation.”

Charlie left soon after and Dean sat there, trying to work up enough courage to place the call he knew he needed to make. He finally hit dial and listened to the phone ring.

“Hello?” He heard Cas answer on the third ring.

“Hey Cas.” He let out the breath he was holding.

“Dean? Are you okay? Its so glad to finally hear from you. I’ve been worried. I’m so sorry if I did something wrong…” Cas rambled before Dean cut him off.

“Cas! Cas, I’m ok. You, uh…you didn’t do anything wrong.” He quickly assured the other man.

“Oh, well…. then what happened? Why did you run out of my house last week?” Cas asked, confusion clear in his voice.

“Well, uh…you see, there is something I should have probably told you about before.” Dean took a deep breath before he confessed. “I’m a virgin.”


	12. Chapter 12

“Well, uh…you see, there is something I should have probably told you about before.” He heard Dean take a deep breath. “I’m a virgin.” _Oh._

“Oh…” Cas uttered, taken by complete surprise at Dean’s confession.

“Yeah…, I uh…I might have freaked out a tad.” Dean chuckled humorlessly; voice laced with insecurity. It made Cas’ heart break for the younger man, remembering how nervous he had been when he was still a virgin himself.

“It’s okay Dean. I can understand why you freaked out now. I’m sorry if I pushed you further than you were ready for.” He apologized, feeling guilty. “I should have asked for consent before I touched you like that.”

“No, no I’m not upset at you Cas. You didn’t push me, it’s, uh, I… Can we talk, like face to face?”

“Of course. Would you like to come over right now? Bianca is at a friend’s house, so we’d have the place to ourselves to talk.”

“Yeah, yeah that sounds good. I’ll be over in like twenty minutes if that’s okay?” Dean sounded relieved.

“Absolutely. I’ll be here waiting.”

They disconnected the call and Cas waited anxiously until he heard a knock on his front door. He let Dean in and they made their way to the couch, leaving space between them. Cas watched Dean wring his hands together, looking uncomfortable, but he didn’t want to push him. He waited the younger man out until he finally seemed ready to talk.

“So, uh… that night… God this is embarrassing.” Dean rubbed the back of his neck; a nervous tell that Cas was becoming quite familiar with now. “When you, uh…touched me, ya know, here.” He waved his hand around his groin area, a cute blush appearing on his freckled cheeks. “I-I kinda…” Dean whispered something that Cas couldn’t make out.

“I’m sorry, I can’t hear you. What was that?” Cas asked.

Dean shut his eyes tight, and with clenched fists he gritted out “I came in my pants.” Cas couldn’t help the small chuckle that escaped his lips.

“Dude really?” Dean looked up to glare at him and Cas held his hands up in apology.

“I’m sorry Dean, I didn’t mean to laugh. Its just…” He chuckled again to himself. “I uh, I had something similar happen to me when I was younger.” He explained, hoping to make Dean feel better about his embarrassment. It was crystal clear now to Cas why Dean had run out that night. It made him feel a lot better about the whole situation now that he knew it was likely just embarrassment that caused this whole situation. That he could work with.

“Really?” Dean quirked an eyebrow, disbelief clear in his voice.

“I’m dead serious. I was…maybe 19 when it happened? Yeah, I think about that age.” He recalled, a small smile on his face at the memory. “I was on a date with a guy I had met in one of my classes and he drove us out to an empty parking lot, obviously planning on getting lucky. I was a virgin myself at the time, and like you, I didn’t tell the other guy. I didn’t even make it to the touching part before I embarrassed myself. Needless to say, that date ended quick and the guy never called me back.” He shrugged as he finished his story. He looked up at Dean and saw a small smile on the other man’s face. “I completely understand why you ran off the other night Dean. But honestly, you don’t need to be embarrassed. I’m pretty sure a ton of guys have had the same thing happen.”

“That, that makes me feel a lot better.” Dean whispered, smiling shyly.

“Good. And thank you for telling me what happened. I’m sorry you felt embarrassed, but if you are willing, I’d like to continue seeing you Dean.” He told the other man, a hopeful smile on his own face.

“Yeah?” Dean breathed out gently in what seemed to be surprised relief and Cas nodded in answer. “You’re really okay with me being a virgin and all?”

“You being a virgin is not a deal breaker for me Dean.” He assured him. “And now that I know, I wont push for anything you aren’t ready for. We can go at your pace. You just tell me what you are comfortable with. I wish I had known before that you have no experience so I knew not to push for anything other than kissing.”

“I-I’m sorry I didn’t tell you. I was just…embarrassed. I mean, I’m a 23-year-old virgin and you’re thirty. I didn’t think you’d want me if you knew.” He said sadly.

Cas reached out and took Dean’s hand in his. “I like you Dean, a lot, and I’m willing to go at whatever pace is good for you. I’m sorry I made you uncomfortable before.”

“Y-you didn’t, not really. I, uh…I liked what we were doing. I was totally into it. It was just…the whole… coming in my pants prematurely thing.” The blush had worked its way down Dean’s neck and Cas found it so endearing. “If you, um…if you’d wanna try again, I’d be cool with it.” He stammered

“Well, I don’t want to rush you Dean.” He said, causing the other man to roll his eyes.

“Ugh, Dude, just kiss me already.” Dean grumbled making Cas chuckle fondly.

“If you’re sure…” He closed the distance between them and pressed his lips against the other man’s gently. He heard him sigh before Dean pressed back into the kiss, tilting his head to deepen it.

The kiss started off slow but quickly heated, both men groaning as they got lost in the moment. Cas could feel his cock harden in his pants but he didn’t want to push for more and have a repeat of last week. Dean seemed to have other ideas. Cas felt him reach a tentative hand up his thigh and Cas pulled back from his mouth. “Dean, we don’t have to do anything besides kissing.”

“I want to.” Dean’s voice was heavy with arousal, and it sent a jolt of arousal straight to the older man’s cock.

“Are you sure?” His own voice was faring no better.

“Yeah, yeah I’m sure. I-I’m not ready for like…um…full on sex.” Dean stammered out, face flush in both arousal and nerves. “But, y-you can touch me l-like last time.”

“Hmm, I have an idea.” Cas offered before pulling Dean on top of him, making the younger man straddle his lap. Dean squeaked in surprise and Cas chuckled. “You can set the pace this way.” He offered in explanation before pulling Dean’s mouth down to his own.

He grabbed Dean’s hips and pulled their groins flush; their hard cocks brushing together through the layers of denim. The younger man moaned and Cas repeated the action, hands guiding Dean’s hips to gyrate on top of him. Dean seemed to get the picture and before long he was grinding in Cas’ lap on his own, his fingers gripping Cas’ hair as their tongues danced together. A particularly sinuous roll of his hips had Cas groaning and gripping the younger man’s lower back tight to him.

“Fuck, Dean…” He moaned aloud.

“God, Cas, I’m gonna…fuck…I’m gonna come in my pants again.” Dean grunted out between rolls of his sexy hips. Every time their cocks rubbed together; Cas felt his orgasm getting closer.

“Fuck, me too.” Cas admitted through gritted teeth, his orgasm was so close and he struggled to hold it back. “Can…can I please touch your cock.” He begged the other man, not wanting them both to end up with a mess inside their jeans.

“Yeah…fuck…yes.” Dean replied heavily, and Cas wasted no time undoing both of their jeans and pulling their hard cocks out, gripping them both tight in his fist. They both moaned loudly as the hot flesh of their cocks touched and Cas began stroking them together. It didn’t take long for the hot come to spurt from their hard lengths, covering his fists in both of their release. They were both breathing heavy, and Dean collapsed on top of him, pinning his come covered hand between them. “Fuck, Cas.”

“Well, I was trying to avoid us getting come on our clothes but too late now.” Cas chuckled through deep breaths.

“Sorry.” Dean whispered, as he buried his head into the older man’s neck. Cas rubbed his clean hand up and down Dean’s back soothingly, knowing the younger man probably needed a few moments to compose himself after his first sexual experience. He didn’t push, content to sit there with Dean in his lap for as long as he needed.

Finally, Dean sat up and looked at Cas with a shy smile on his face. “That, um…that was nice.” He said finally, looking absolutely adorable. Cas just smiled up at him.

“Yes. It was.” He agreed.

Dean climbed off of his lap and sat beside him as they both tucked their softening cocks back inside their jeans. Cas reached over on the end table for a tissue and wiped his hand the best he could.

“I have a shirt you can borrow to change into.” He offered, pointing to the drying come on Dean’s shirt. The other man looked down and laughed.

“Well, at least it wasn’t inside my underwear this time. That was a _very_ uncomfortable drive.” He joked, and Cas was glad to hear that he didn’t sound uncomfortable this time.

“I can imagine.” He smiled. “I’ll be right back with a shirt.” He stood up and went to his bedroom and quickly changed out of the cum stained shirt, making sure to grab another one of his smaller ones for Dean. When he went back out to the living room, the other man had already taken his shirt off and Cas stopped in his tracks as he took in the trim body in front of him. When Dean looked up at his return, he quickly shook himself out of his ogling and threw him the shirt which he was quick to put on.

“Thanks Cas.” Dean said sincerely. “And uh, thanks for being cool with the whole, ya know…virgin thing.” He gestured at whole body and Cas just waved him off good naturedly.

“Its really not a problem Dean.” He assured again as he sat back down and patted the seat next to him which Dean quickly occupied. Cas put his arm around the younger man’s shoulders as he kissed the side of his head. “Would you like to watch a movie?” He asked, not wanting their night to end quite yet.

“Sure.” Dean replied as he cuddled against Cas’ side, filling Cas with warmth as they settled together comfortably. He sighed in contentment, glad they had cleared the air and were moving on from last week. He felt hopeful again that things would look up from here.


	13. Chapter 13

February had turned into March, which quickly became April and things between Castiel and Dean were pretty good. After they cleared the air about Dean’s little… _problem_ , he guessed you could call it, things had been much smoother sailing. Cas had apologized for their little tryst on the couch, saying he shouldn’t have gotten carried away without thinking of using protection. Dean hadn’t even realized you even needed a condom for what little they did. That had been a fun conversation, he cringed at the memory.

_“But no one even stuck anything in anywhere Cas”_

_“It doesn’t matter Dean. Bodily fluids were involved. There is still a risk.”_

_“You got a disease I should know about? Cuz I’m a virgin so its not like I’m gonna give you the clap or something.”_

Cas had just rolled his eyes in annoyance before insisting they both get checked out for STIs and Dean reluctantly agreed. That ended up being probably the most awkward doctor visit of his life. He still couldn’t look at a q-tip without shuddering after getting the inside of his junk swabbed. Luckily, they had both been disease free. They had had a few more make out sessions on the couch, but they still hadn’t gone any further than jerking each other off.

They had gone out on a few more dates over the last two months; Once to the movies, and another time out for dinner. It wasn’t easy though, for them to plan time just the two of them, and Dean was quickly learning what it was really like to date a man with a kid. As he reassured Cas on multiple occasions, he really didn’t mind though. He had known going into this that the two were a package deal, and that his daughter would always come first. That meant that Cas was frequently busy with all sorts of extracurricular activities; Girls Scouts, dance, and kids parties took up much of the other man’s time, so they were mostly relegated to dates involving Bianca. Which is why they were currently at the park, watching the little girl play as they sat on a bench together. Dean smiled as he watched her jump from the swing and land in the sand, while Cas was apologizing again for about the thirtieth time.

“I’m sorry Gabe had to cancel last minute.” The regret was clear in his voice. They had originally planned to go to a comedy club for an early afternoon show, but Gabe got called into the bakery he owned with some last-minute problem he had to take care of, so they had no one to watch Bianca.

“Cas, we’ve been over this already. Its fine. There is nothing to apologize for.” He insisted again. “I really don’t mind having your daughter with us.”

“I know you said that, but I still feel bad Dean. This is not exactly the most exciting place for a date.” He said bitterly, and Dean reached for Cas’ hand, covering it with his own before lacing their fingers together.

“As long as I’m spending time with you, it really doesn’t matter.” And he was being completely honest. He loved spending time with the older man, regardless of what they were doing. It was so easy to just be with him. They rarely had any awkward moments anymore, the more time they spent together. It was just so easy to become comfortable around Cas. And Bianca made him laugh on a near constant basis. He had come to really care about the little girl, more than he ever cared for any other kid he’d been around.

“I feel the same way.” Cas smiled shyly, before he cleared his throat, looking a little nervous to Dean. “I was wondering…. we’ve been dating for two months now, right?”

“Yeah.” Dean nodded, curious about where this conversation was about to go.

“And I think things are going well. Don’t you?” Cas asked.

“Very well.” Dean agreed, squeezing Cas’ hand in reassurance.

“Okay, so…I uh, I was wondering if you would want to make it official?” Cas’ voice lifted in question; He looked uncertain as he waited for Dean’s reply.

“Wha-what do you mean by official?” Dean said hesitantly, causing Cas to make a frustrated noise in his throat.

“Remember when Bianca asked if we were boyfriends, and we said not yet?” Dean nodded in reply, hope blossoming in his chest at what he thought was coming next. “Well, I’d like to be able to tell her yes now.” Cas divulged; The butterflies in Dean going haywire.

“Th-that sounds good.” Dean choked out around the lump in his throat. “I’d uh…I’d like to be your boyfriend.” He answered softy, while his insides were screaming for joy. He couldn’t help the smile that continued to grow on his face, and the warmth that spread through him. _He_ had a boyfriend. He had a _boyfriend!_

“That makes me very happy.” Cas whispered back; the gummy smile on his face replacing the uncertainty that was there before. That smile made Dean lo- _like_ him even more. Fuck. It was way too soon to be even thinking of the L-word yet.

“Did you think I’d say no?” Dean said teasingly, trying to lighten the heaviness he was feeling in his chest.

“I wasn’t completely sure you wouldn’t think it was too soon.” Cas shrugged.

“Definitely not Cas.” He told the other man as they gazed into each other’s eyes, smiles so wide now that Dean’s face was beginning to hurt. Luckily, Bianca ran over to interrupt their staring.

“Dean! Dean! Did you see me jump so high!” She beamed excitedly before looking down and noticing their joined hands. He could see the gears in her head turning as she processed that, and Dean knew what she was going to ask before she even said it. “So, are you boyfriends yet?”

This time, there was no stammering or blushing. Dean and Cas just looked at each other with a smile before Cas turned back to his daughter.

“Yes, we are boyfriends now.” He affirmed for the little girl.

She whooped and threw her fist in the air before yelling “Yes! I’m gonna have two dads now!”

“Oh, dear _god._ ” Cas blurted out before covering his face with his free hand, and Dean just threw his head back in laughter. There was never a dull moment with that girl.

Cas eventually calmed his daughter down from her happy dance and explained to her that just because they were boyfriends, that doesn’t mean they were getting married. That had been slightly awkward as Cas stuttered his way through, but she seemed to take it well, before she ran back over to the swings to play again.

That night, after he got into bed, Dean had a sudden realization. He had a boyfriend now. That meant he finally had a _reason_ to come out to his parents. _Shit._ He was soooooo not looking forward to that.


	14. Chapter 14

Dean’s stomach had been in knots all day- _hell_ -all week. After they had decided they were now in an actual, official, full-on relationship, he knew he finally had to grow a pair and come out to his parents. He still couldn’t believe he had an actual boyfriend now. It was one thing to date the man, but for Cas to want an actual relationship with him? Dean was still kind of in shock. It felt serious now. It would have been different if Cas was younger like Dean; the boyfriend label probably wouldn’t feel as significant. But Cas was a grown man with a child. He didn’t just jump in to a relationship without some serious consideration. He had made that extremely clear right from the beginning. So, now that they were actually official and the relationship was getting more serious, he knew it was time.

That didn’t mean he felt ready though, oh no. Totally the opposite. He felt like he was going to throw up every time he thought about it. He had so many emotions running through him that it was hard to wade his way through the river of his feelings. There was fear and terror. There was anxiousness and hope. He was a jumble of nerves, not knowing how they would react. Would they accept him? Or would they disown him like Cas’ parents had? Maybe they would even tell him they loved him but didn’t want to see any of his relationships in their face. There were so many possibilities of how it could go down, that he was making himself crazy just imagining them.

Fuck it. He would just have to push through and get it over with. No sense wasting time worrying. He just needed to rip off the band aid. He gave himself a quick last-minute pep talk and made his way down the stairs and into the Livingroom where his parents were seated, watching the news. He stood in the entranceway, taking a few deep breaths to psych himself up, before his mom looked up and noticed him standing there.

“Hey sweetie. Is everything okay?” She asked in concern. She could probably see the anxiousness on his face, and feel the stress pouring off of him.

“Uh, y-yeah. Yeah. I…um…I just need to talk to you guys about something.” He stammered, wringing his hands together nervously.

“Come sit down hon. What is it?” She asked.

He walked into the room and took the loveseat across from them. His heart was racing and his palms were sweating. His head was down, eyes staring at the carpet and he couldn’t bring himself to look into their faces just yet.

“What is it son?” His dad asked. Dean could even hear the concern in his father’s voice and it helped ease his anxiety slightly.

“I… I’m….” He started before he had to swallow around the lump in his throat. “I…I have something I need to tell you.” He whispered at the floor.

“What is it sweetheart? You know you can tell us anything.” His mom assured him and he smiled sadly.

“I, I’m not really sure how you’re gonna take it.” He confessed quietly.

“Please don’t tell us you got a girl pregnant.” His dad begged which caused a small chuckle to escape his lips.

“Ah no. No, you um… you don’t ever have to worry about that.” He chuckled bitterly before taking a deep breath. He felt like he was skydiving, and about to pull the ripcord, and he praying it would open so he wouldn’t come crashing to the ground.

He closed his eyes before finally confessing “I-I’m…I’m gay.” There, it was out there now. He was shaking inside, waiting for their reaction. He couldn’t bare to look up into their eyes, fearing he would see rejection written all over their faces. He suddenly felt the couch dip beside him and an arm wrap around his shoulder.

“Dean, son…look at me.” The gentle command had him following, and he looked up into his father’s eyes. He was expecting disgust or anger, but he only saw a gentle smile. “You are my son and I love you. Nothing, and I mean _nothing_ , could ever change that. Do you hear me?” The tears that had been welling in his eyes began to slowly fall down his cheeks at those words. He threw his arms around his dad’s neck and let loose the sob that he could no longer hold back. He felt his mom sit down on his other side and join the hug.

“Your father and I don’t care who you love. The only thing that matters is that you are happy sweetheart.” She told him as she kissed the back of his neck. His body shook with the tears that were now streaming down his face. He had been so terrified that they wouldn’t love him anymore, especially his father who rarely showed any kind of tenderness. So, for him to be the first to tell Dean he loved him no matter what, made Dean throat thick with emotion. He felt so blessed to have parents that accepted him for who he was, no matter that he was gay.

He stayed wrapped in their arms until the tears finally stopped and he moved to sit up, ending the family hug. He reached his hand up to wipe away the wetness on his cheeks. “Th-thank you.” He managed to choke out, voice hoarse from crying.

“Did you think we wouldn’t accept you?” His father asked, sounding hurt, and Dean felt guilty for making him sound that way.

“I, uh...it’s just, I didn’t… I didn’t know…” He stuttered, not knowing how to explain himself. “I was scared…” He confessed, voice barely above a whisper.

“I’m sorry if I ever gave you the impression that I wouldn’t accept this part of you son. You can date whoever makes you happy.” He looked up at the anguish in his father’s voice. He even saw John’s eyes mist over and he hugged his dad again.

“You didn’t dad. I…it’s just, you don’t know how terrifying it is to have to…to have to come out. My boyfriend’s parents disowned him when they found out.”

“Boyfriend?” His mom’s voice perked up questioningly.

 _Shit_. He hadn’t meant to tell them about Cas yet. He was trying to do this one thing at a time. Guess the cat was out of the bag now. He sat back up straight and rubbed a nervous hand over the back of his neck.

“Um…yeah. Yeah I have a…ah...a boyfriend.” He blushed, nervous about having to now tell them he was also dating an older man; a man with a _child_.

“Who is he? What’s his name? What is he like?” He mom blabbered excitedly. His Dad just rolled his eyes.

“Calm down, Mary. One question at a time for the poor boy.” He teased his wife.

“Sorry. I’m just so excited my boy has someone!” She apologized.

“Its fine Mom. Um… his name is Cas.”

“How did you two meet? Was it as school?” She prodded.

“Well, he uh, we actually met last summer at the college fair. “He hoped giving her as little information as possible would be good before he could slowly work his way up to giving her more. Of course, she wouldn’t be thwarted in her quest for all of the details though.

“Oh, was he another student volunteer?”

“Not exactly. He uh, he was there with his daughter.” He admitted, holding his breath for their reaction to that little bomb.

“Daughter? Dean, how old is this man?” His father asked gruffly.

“…Thirty.” He managed to squeak out.

“Thirty! What the hell does a 30-year-old want with a twenty-three-year-old?” His father barked loudly, making Dean hunch his shoulders like a chastised child.

“John!” His mother cut in “Knock it off!” She reached over to smack him upside the head. “Calm down for Pete’s sake. Dean is an adult.” She scolded.

“But…” His father began in protest before stopping at the look on her face.

“Our son has the right to date anyone he chooses. Didn’t you just tell him that?” His father looked properly chastised before he sighed.

“Fine. Yes, you are an adult and can make your own choices.” He grudgingly agreed. “But I want to meet this man.” His voice was stern.

“Yes, I would too. Why don’t you invite Cas and his daughter over for dinner next weekend? Then we can all be properly introduced.” His mom suggested happily.

“Okay, I’ll, uh… I guess I’ll ask him.” He hesitated to agree. He had barely gotten through the whole ‘coming out’ part and was now being thrust right into the ‘meet the parent’s’ part without a second to breath.

“Good, now that that’s settled, who wants some ice cream?” His mom asked cheerfully, and Dean was glad for the change in subject. At least everything went much better than he had expected, even if he now had to introduce Cas to them much sooner than expected. Now he just had to get the nerve up to ask Cas to dinner. Hopefully he wouldn’t scare off the poor man.


	15. Chapter 15

Cas was sitting at a table in the corner of the café, sipping on his chamomile tea. He was trying to tune out his brothers incessant teasing, but he was having no luck. Why did he think this was a good idea again?

Gabe had been pestering him for awhile now to meet Dean, pretty much since they had begun dating, and now that they had taken the next step, Cas figured it was probably time. He was dreading it though. He loved his brother, he really did, but the man was a lot to handle. He was praying that he didn’t scare Dean away.

“So, when’s the boy toy getting here?” Gabe prodded as he popped a lollipop into his mouth. Cas was shocked the man had any teeth left, considering the amount of sugar he consumed on a regular basis.

“He should be here any minute Gabe.” Cas sighed before looking at his brother sternly. “And you will not embarrass me or I’ll tell Kali about that weekend in Reno.” He threatened the shorter man.

“Okay, okay, geeze! Chillax Cassie. I’ll be on my best behavior.” He gave a mock salute, that had Cas rolling his eyes. Just then, the front door chimed and in walked his boyfriend. He watched Dean look around before catching Cas’ eye, and the younger man made his way over to their table, a grin on his face.

“Heya Cas.” The young man greeted as Cas stood up and leaned in to kiss his boyfriend, causing a blush to appear on his freckled cheeks. Cas loved putting that blush there.

“Hello Dean.” He greeted. “I’d like you to meet my older brother, Gabriel. Gabriel, this is Dean.” He introduced the two men as they sat down at the table.

“Nice to meet you.” Dean held his hand out for the other man to shake. Gabe just looked at the offered hand and smirked.

“No offense, but I’m sure that hand has probably touched my bro’s dangly bits.” He teased, making Cas groan in frustration. He knew this was a bad idea.

“Gabe!” He scolded through gritted teeth.

“Kidding, kidding!” He took the offered hand and shook it. “Sorry my brother always has a stick up his ass. Although, I’m sure you could think of something to replace it with.” He winked, making Dean choke on air. Thankfully, Cas had warned Dean ahead of time about his brother’s crude humor, and Dean recovered quickly.

“Cas wasn’t kidding about you ,huh?” He chuckled.

“I’m so sorry Dean. My brother has absolutely no filter.” Cas apologized; annoyance clear in his voice.

“Eh, no biggie. You’ve met Charlie. She lacks a filter most of the time too.” Dean shrugged with a smile. “So, Gabe, you own this place?”

“Correctamundo. This is my little slice of heaven.” Gabe bragged.

“I’m guessing that’s why you named it Slice of Heaven Café?” Dean quirked a teasing eyebrow.

“Pretty and smart? Man, you hit the jackpot with this one.” Gabe teased right back making Dean laugh. Cas’ shoulders relaxed a bit, now that it seemed Dean wasn’t taking any offense at his brother’s words.

He listened to the sarcasm being flung back and forth between the two and before long they were both laughing together. Gabe had the waitress bring over coffee for them and they drank while they talked. Somehow the conversation turned to the most ridiculous gay one-liners they had ever heard.

“I don’t know how you two do it, being gay. Life without women would be a pain in the ass, literally.”

“Did you hear about the new gay sitcom coming out? It’s called ‘Leave it, It’s a Beaver.’’’

“I was going to make a joke about homosexuality, butt fuck it.”

Cas just rolled his eyes at the two of them, but at least they were laughing and getting along.

“Alright, I think we’ve heard enough jokes.” He butted it. “I need to pick up Bee from school soon so I think we are finished here.” He stood up and the other two followed. He walked Dean out to his car and kissed him goodbye.

“Hey, um…” Dean began, a nervous tone to his voice. “So…I came out to my parents yesterday.”

“Wow. That’s huge. How did it go?” Cas asked, hoping it went better than his own coming out had.

“Good, they uh…they were really supportive.” Dean smiled and Cas felt relief for the younger man.

“Oh, Dean I’m so glad to hear that.”

“Yeah, me too. They, um…they want to meet you. Said to invite you over for dinner next Sunday. You and Bianca.”

“Oh…” Cas said in surprise. He wasn’t expecting to have to meet the parent’s so soon. But since Dean had met Gabe, he guessed it was only fair. “Okay, we’ll be there.”

“You sure? I Know its soon and everything. But I let it slip that I had a boyfriend, so they started asking all about you and everything and saying they want to meet you- “

“Dean! Slow Down.” Cas cut in with a fond chuckle. “I’d love to meet your parents.” He assured the younger man. Dean’s shoulders slumped in relief.

“Okay, okay good. So, I guess I’ll text you later?”

“Of course.” He kissed Dean goodbye and made his way back in the building to say goodbye to his brother who had apparently been waiting for him.

“I like him Cassie. He seems really good for you.” His brother said sincerely, and the honesty in his voice threw Cas for a moment. It was rare his brother was ever serious about anything, always making a joke out of every situation. To hear his brother, speak so sincerely now made Cas’ heart fill with warmth.

“I really like him too Gabe.” He agreed softly, feeling happier than he had felt in a long long time.

“Don’t let him get away.” Gabe patted his back before walking back behind the counter, leaving Cas to stand there and think about his brother’s words. He vowed to make sure he did everything in his power to keep Dean in his life.


	16. Chapter 16

** **

Dean stood on the porch and knocked on the front door. Cas had invited him over for a movie night date. Bianca was sleeping at a friend’s house, so they had the whole house to themselves and Dean was nervous. This would be the first time he had been over the older man’s house without his daughter there as a buffer. The most they had done so far was quick hand jobs when she went to sleep, but now that they didn’t have to worry about being interrupted, the possibility of going further was all Dean could think about.

He knew Cas wouldn’t pressure him for more; he had made that clear after the first time. But Dean wanted more. Maybe not a home run, but he was at least hoping to get to third base. Lately, every time he looked at Cas’ lips, he couldn’t help but picture what they would feel like wrapped around his hard cock. And when he got quick glimpses of the other man’s dick during their rushed quickies, he imagined sinking to his knees and having Cas push his hard length between Dean’s own lips. He didn’t know which he wanted more; he wanted them both, and he hoped they would get there tonight.

Cas answered the door and Dean took a moment to drink in the sight of his boyfriend. The older man was dressed in a pair of tight jeans that had his meaty thighs on full display. Dean wanted to feel them wrapped around his head as he went down on him. _Fuck_. He had to stop with these thoughts before he popped a boner too early.

“Hello Dean.” Cas greeted, grinning happily at the sight of Dean.

“Hey Cas.” Dean leaned in and kissed his boyfriend chastely before they made their way into the house.

He took his jacket off to hang on the hook beside the door, and as he turned around, Cas was on him, pushing his back against the door and taking Dean by surprise. He captured the younger man’s lips in a kiss much more heated than before. His lips made their way up Dean’s chin and neck till he captured the lobe of his ear between his teeth.

“Fuck, Dean…” Cas growled into his ear, sending a shiver of lust down his spine. “I’ve been thinking about you all day.”

“M-me too.” Dean groaned as Cas pushed his thigh between Dean’s legs, grinding up against his quickly hardening cock. “More…fuck…I want more.”

“What do you want Dean? Tell me.” Cas said before capturing his lips in another kiss. Dean’s head was spinning as he was kissed to breathlessness before the other man pulled back.

“I-I…want…. I want mouths.” He could barely get words out as Cas kept grinding against his hard dick.

“You want me to suck your cock?” Cas replied wickedly as he licked the shell of the younger man’s ear, making Dean whimper. He nodded in response, too lost in pleasure for words.

Cas dropped to his knees in front of Dean and made quick work of his buckle, before he unzipped his jeans and palmed over the bulge in Dean’s briefs.

“F-fuck.” He whimpered as Cas pulled his hard cock out and gave it a few tugs. His eyes were shut tight in pleasure and he felt a tongue lick the underside of his cock from base to tip. His knees buckled; Cas’ strong hands pinning him to the door were the only thing that stopped him from falling. He heard a dark chuckle before his cock was surrounded by the hot wet heat of Cas mouth, as the older man took him to the root.

“Fuck! Cas…” He moaned as his cock was deepthroated. His boyfriend bobbed his head up and down his hard length, his tongue wrapping around the head at each pass. His toes curled as Cas flicked his tongue just right under the head of his cock, before pushing it into the slit of his dick. “God, your f-fucking m-mouth.” He moaned, hand reaching out to grab a fist of Cas’ hair.

Cas pulled back to look up at Dean. “Fuck my mouth.” He instructed, voice deep with arousal, before taking Dean’s cock back inside. Dean wasted no time complying, thrusting his hips forward into the tight throat of the man below him. Cas made a small choking sound, and Dean was about to pull back, but Cas reached up and grabbed his hips and pulled him forward again, making it clear he didn’t mind the rough treatment.

Dean thrusted over and over between Cas’ plush lips, feeling his orgasm building quickly. He felt Cas gently squeeze his balls as he thrusted deep into his throat and that was what tipped him over the edge. He was coming in Cas’ mouth before he had a chance to warn him, but from the deep moan Cas let out, he didn’t seem to mind. His body shook as he emptied into the other man; Cas sucking and licking him through it before the pleasure became too much and Dean gently pushed his head away. He was panting, trying to catch his breath as his knees finally gave out, and he slid down the door, landing on his ass in front of Cas.

“Holy fuck.” He managed to pant out as he looked at his boyfriend’s face. Cas’ hair was sticking up everywhere from Deans hands gripping it, and he looked the picture of debauched. He watched Cas push down his own pants to pull his cock out and he began stroking it. Dean’s brain finally came back online and he reached out to stop Cas.

“I wanna suck you too.” He told him, causing Cas to groan. He pushed Cas to lay back on the floor before taking the man’s hard cock in his own fist. He gave it a few long strokes before sticking a tentative tongue out to lick the head where pre-cum had beaded. It tasted a bit salty, but not too bad, so he licked the head again, humming appreciatively in his throat. He heard Cas moan and it spurred him on to go further. He wrapped his lips around the head and sucked hard, making the other man whimper in pleasure. He took him down as far as he could, about halfway down, before he felt his gag reflex kick in and had to pull back. He definitely needed to practice before he’d ever be able to deepthroat like Cas.

He wrapped his hand around what he couldn’t fit in his mouth and stroked as he bobbed his head up and down the hard cock.

“Fuck Dean… yes...” Cas moaned, as Dean sucked and licked his boyfriend’s cock, alternating between deep and shallow bobs of his head. He heard Cas’ breathing pick up and he tried to pull Dean’s head away. “Dean, I’m gonna cum.” He warned, but Dean didn’t stop. He was suddenly desperate to taste the man’s come, and he was incredibly thankful at Cas’ foresight to get them tested so they could do this. Cas tensed up and then ropes of hot, salty cum were filling Dean’s mouth. It wasn’t the best taste but just knowing it was Cas filling his mouth had him groaning in pleasure as he swallowed it down.

They both took a minute to calm down from their pleasure before they tucked themselves back in and helped each other off the ground. They made their way to the couch where Cas pulled Dean to lay on top of his chest and held him close.

“How are you feeling Dean?” His boyfriend asked as he ran his fingers through Deans short hair.

“Fuck Cas. Th-that was amazing.” He breathed out, still high on pleasure.

“I’m glad you enjoyed your first blowjob.” Cas chuckled fondly at him.

“Um…did I do okay?” Dean asked uncertainly, feeling self-conscious of his inexperience.

“You were great Dean. Your mouth felt amazing, sweetheart.” Dean felt warmth spread through his body at both the praise, and the endearment Cas slipped out. He tucked his face into his boyfriends’ neck and sighed happily, feeling more content in that moment than he had ever felt before.

He must have still been drunk on endorphins, because before he could think on it, he blurted out “I wanna have sex.”

He felt Cas tense up for a moment before he sat up, dislodging Dean from where he had been comfortably laying. “We just had sex Dean.” He tilted his head in confusion. Dean knew he had to be beat red in embarrassment but since he already blurted that out, he might as well push on.

“That was just a blowjob Cas. I mean like _sex_ -sex. You know, the _real thing_.” He emphasized the word, hoping Cas understood what he was saying.

“Dean. All sex is the real thing. Blowjobs are still sex.” Cas insisted causing Dean to roll his eyes.

“I mean like actual full on sex Cas. You know…” He waved his hands in a crude manner, trying to mime what he was talking about.

“You’re referring to anal?” Cas asked bluntly, causing Dean to choke on air at the matter-of-fact way Cas stated it.

“Y-yeah, that.” He said dumbly.

“If that’s something you’d like to do, I’m absolutely on board. But you know we don’t actually have to do that right? That just because we’re gay, that doesn’t mean we have to engage in anal sex. There are a lot of couples that never do.” Cas explained, making Dean’s eyebrows shoot up in surprise.

“Wait, Really?” He asked confused. Cas just sighed.

“Yes, really. A lot of gay men don’t even like anal. It’s actually way more common than society makes it seem. The porn industry really is to blame in my opinion. The whole industry puts unrealistic expectations and thoughts into people’s head about what gay sex is really like. In reality, blowjobs and frottage and things like that are way more common for gay men to engage in with their partners. Anal is not the be all, end all of sex. Don’t get me wrong, it is definitely something I enjoy, but it’s a personal preference.” Cas finished his whole speech, leaving Dean gaping like a fish before he was finally able to reply.

“Oh, I…uh…I didn’t know that.” His shoulders hunched in shame at his own stupidity. He always thought anal was just something every gay guy did.

“Sorry for my rant, I just didn’t want you to think it was something you are required to do.” Cas reached out to squeeze his hand and Dean smiled at the thoughtfulness of his boyfriend. “Is it still something you wish to try?”

He thought about it. Did he really want to try it? He knew porn wasn’t exactly accurate, but it always seemed like it was pleasurable. “Um…yeah. I uh, I do. It probably sounds dumb but, I feel like if I don’t than I might be missing out, ya know? But I do have, uh questions.” He inwardly cringed at himself. It was true he did have questions, but he knew this was going to be an awkward conversation. He really didn’t want to have to ask, but he knew Cas wouldn’t laugh at him, and like they always say “If you can’t talk about it, you shouldn’t be doing it.”

“What questions do you have? I’ll try to answer anything you want to ask.” Cas said kindly, smiling as he held Deans hand.

“Okay, this is probably gonna be Hella awkward, just so you’re warned.” He pointed a finger at Cas, making the other man chuckle.

“Sex questions usually are.” He agreed.

“Okay, so…does it hurt? You know being the receiver?” Dean asked, blushing through the question.

“It can, sure. But if you have a caring partner it shouldn’t be too bad. The first time is definitely more likely to be painful. But if we do it, I’d make sure to stretch you out properly first so you’d feel as little discomfort as possible.” Cas told him; sincerity clear in his voice. Just the thought of Cas stretching him out had him flushing and his spent cock tried to twitch in response.

“Okay…next question.” He continued, rubbing his neck in embarrassment. “Is it messy?” He wrinkled his nose at the thought. That was the thing he was actually most concerned about. He had already figured it could be painful, but he would be mortified if they did it and there was a mess.

Cas laughed quietly “That depends. And this is another thing that never gets talked about either and why porn and writing are sometimes incredibly unrealistic. Obviously, the anus is meant for waste. So yes, it could be messy. Which is why anal is typically planned ahead of time, and not something done spur of the moment. I personally always use a douche if I know I’m going to bottom that night, and I wouldn’t eat heavy that day either. Its definitely not all sexy, the planning that goes into it, which is why its not always done, blowjobs and such are more common.” Cas explained clearly to him. He felt so much love for the man in front of him in that moment. Yes, Love. He was able to admit it to himself, he was definitely in love. But it was still too soon to say out loud so he’d keep that little secret for himself. But he felt so much love for Cas, that he would sit here and explain in detail all the awkward and messy parts of sex, just because Dean had questions.

“Okay. I, uh…I think that’s all I have. Thanks for, ya know, explaining it and stuff.” He was still embarrassed at the conversation, but at least know he knew what he needed to know.

“So, after all of that, you think you still wanna try?” Cas asked curiously.

“I-I do. Maybe, uh, maybe next time we have a night to ourselves?” Dean asked unsurely.

“That sounds good. Maybe after we have dinner with your parents on Sunday, I can drop Bee off at Gabriel’s to sleep, and you can come over and spend the night?” his boyfriend suggested.

“Yeah, th-that sounds like a plan.” He agreed.

The rest of the night was spent laying together on Cas couch watching Star Wars, both of their favorite movies. When Cas walked him out and kissed him goodbye, he was suddenly very anxious for the week to pass and Sunday to come.


	17. Chapter 17

“Hurry up Bee! I don’t want to show up late!” Cas yelled up to his daughter who was taking her sweet time getting ready. He patted his pockets, making sure he had everything, before he took one last quick look in the mirror. He looked good, like a proper presentable boyfriend. He was so anxious about meeting Dean’s parents tonight, and he really hoped he would make a decent first impression on them. Dean had warned him that his father had reservations about him dating an older man with a child; Cas understood where he was coming from, being a parent himself. He couldn’t really blame John for being overprotective; He’s sure he will be too once Bee gets older.

He finally heard his daughter’s loud footsteps trampling down the stairs and he just rolled his eyes. No matter how many times he told her not to, she always ran down those damn stairs.

“I’m ready papa!” She exclaimed cheerfully, as she stomped into the room in a pair of boots, he didn’t remember buying her, which could only mean his brother had probably taken her shopping the last time he watched her. Gabe did love spoiling his niece. She was starting to look less like a little girl each day and he missed it. He shook himself out of his melancholy thoughts and steered his daughter to the car so they could make the short drive over to Dean’s house.

“Remember to be on your best behavior okay Bee? This is the first time we’ve ever been invited to meet someone’s parents and I want to make a good impression.” He instructed her as he pulled up to the house and turned the ignition off.

“I promise papa. That’s why I’m wearing my new pretty boots today” She replied, making Cas smile fondly. He loved his little girl.

They left the car and walked up to the house, Cas carrying a bottle of wine to give his hosts. He knocked on the door and waited anxiously for someone to answer. The door opened, and a woman answered, Dean’s mother Cas assumed.

“Come in, come in,” She moved to the side to let them enter. “Thank you for coming. Let me grab your coats.” She offered, hanging them up on a hook by the door. “I’m Mary and you must be Cas.

“Yes, I’m Castiel.” He nodded, holding his hand out to shake. “Cas for short.” The shook hands and then she turned to look at his daughter.

“And what’s your name sweetie?” She asked kindly.

“My name’s Bianca but papa calls me Bee.” She smiled, rocking back and forth on her heels.

“That’s a lovely name. Perfect for a pretty girl like you.” Mary said sweetly before ushering them into the living room. “Dinner should be ready soon. Why don’t you make yourselves comfortable while I call the others down.”

“Thank you, Mary. Here this is for you.” He handed her the bottle of wine he was holding.

“Oh, thank you. You didn’t have to bring anything.” She took the bottle and walked to the kitchen, yelling up the stairs for Dean to come down. Cas heard footsteps coming down the stairs and then Dean turned the corner.

“Heya Cas. Hi Bee.” He smiled as he made his way over to them.

“Hello Dean” Cas replied, kissing Dean’s cheek and making him blush and Bianca giggle like she always did when Cas and Dean kissed.

“I hope my mom was okay. She didn’t scare you away yet, did she?” Dean asked, a nervous chuckle in his voice.

“She was very sweet Dean.”

“Just wait till my dad starts in.” He grumbled.

“I see our guests have arrived.” A man’s voice came from the other side of the room, making Cas turn to look. The man was tall, dark haired, and had a stern look on his face. Cas assumed this must be Dean’s father, John Winchester. The “Speak of the Devil.” Dean whispered assured him he was right. Cas stood up to greet him properly.

“I’m Castiel Novak. You must be John.” He held his hand out to shake, and John took it, squeezing firmly in a show of strength as he assessed Cas.

“Nice to meet you.” John said, his unsmiling face making sweat bead down the back of Cas’ neck. Dean had not been lying when he said his Dad could be intimidating.

“You too, Sir.” He was glad his voice didn’t shake like the rest of his insides were currently doing. John stared him down for a few moments before releasing his hand and moving to sit on the recliner in the room. The rest of them followed suit, Cas and Dean sitting on the couch with Bianca between them. They sat in awkward silence until Bianca interjected.

“You don’t look that old.” She stated, her head tilted in consideration. Cas noticed John’s lip twitch before he schooled his features.

“Oh no? Did you expect me to look old?” He asked her.

“Well, yeah. Papa and Dean are boyfriends, and since your Dean’s daddy I thought you’d be super old.” She blurted out, and Cas cringed at his daughter’s lack of filter.

“Hm, well your Papa is a lot older than Dean. And I’m not that much older than your Papa.” John remarked, looking at Bianca, while clearly directing that statement as a jibe at Cas. This was not going well. It was clear Dean hadn’t been exaggerating his Father’s disapproval at how old Cas was.

“Is that true Papa? You’re a lot older than Dean?” His daughter turned to him in question.

“Y-yes Bee. I’m um… eight years older than Dean is.” He squirmed in his seat, uncomfortable at the scrutiny he could feel coming off John.

“Oh wow! That’s how old I am. So, when you were my age, Dean was just a baby!” She exclaimed in awe, and Cas wanted to die right on the spot. This conversation just kept getting worse and worse. Thankfully, he was saved from having to reply by Mary calling them all to the table. Cas quickly guided his daughter into the kitchen and they all sat down. A young man was already at the table and looked up as they sat. He looked a bit younger than Dean, with shaggy brown hair.

“You must be the boyfriend.” He smiled at Cas. “I’m Sam, Dean’s brother.”

“It’s nice to meet you too.” He replied politely “I’m Castiel.” He introduced himself. “This is my daughter Bianca.”

“Hi.” His little girl waved shyly to the young man,

“Hi Bianca. Dean told me you are in third grade this year. How do you like school?” Sam asked, which lead Bianca to start babbling all about her class and all of her friends, and soon the atmosphere lightened up as the adults smiled and chuckled at her theatrical storytelling.

Dinner went pretty well from there, Cas getting asked the normal questions he expected; what does he do for a living, where does he live, etc., and before long, they finished eating and made their way back to the living room to hang out for a bit. Cas was in the middle of talking to Sam about computers when he heard Mary address his daughter.

“I love your boots. They are so fashionable.” She cood at Bianca, and the little girl smiled before she looked at Mary with a serious face.

“I made extra sure to wear them tonight so we could make a good impression.” She said with as much confidence as an eight-year-old can.

“Oh, well that was smart of you.” Mary told her, biting back a laugh. “And why did you want to make a good impression?”

“This is our first time at a big family dinner. We want to make sure we get invited back. Right Papa?” She turned to her father, and Cas’ heart broke, knowing that his daughter even realized just how important this was to him.

“You’ve never had a family dinner?” Mary gasped surprised.

“Nope. I don’t have any grandma or grandpas, just Uncle Gabe. But if my papa and Dean gets married, you can be my grandma.” Bianca announced happily, making Cas choke on air, and sputter. He thought he’d nipped the marriage conversation in the bud already, but apparently Bianca would not be deterred.

“Bianca!” He hissed quietly at her.

“Oh, sorry papa I forgot I’m not supposed to talk about that cuz you only just started being boyfriends.” She smiled innocently, and Cas couldn’t really be upset with her. There was awkward silence in the air, no one knowing quite what to say, before Mary cleared her throat.

“Well, you can come over here for dinner anytime Bianca. We’d love to have you.”

“Really?” She asked, beaming. “That would be great. I loved having dinner here. Its always so quiet at my house.” She said, a pout on her pretty face.

“Of course, sweetie. Hey, why don’t we go in the other room and color while the boys talk for a bit?” Mary stood and held her hand out for Bianca who took it and followed Mary out of the room, skipping along besides her. Now that Bianca wasn’t there as a buffer, Cas’ nerves came back in full force. He felt Dean shift closer on the couch and grab his hand, squeezing it in reassurance before a throat cleared across the room. He looked up into the intimidating gaze of his boyfriend’s father.

“So, Castiel… what are your intensions with my son?” He asked gruffly and Dean groaned beside him.

“Come on Dad.” He whined “Do we really have to do this?”

“I just want to know why a thirty-year-old man with a kid wants to date a twenty-three-year-old college student.” John crossed his arms as he stared Cas down.

“Dad, come- “Dean started before Cas held his hand up and interrupted.

“It’s fine Dean.” He told his boyfriend with a smile before turning towards the older man.

“I know you have an issue with my age, and I get it, I really do. I’m a parent too and if I was in your shoes, I’d feel the same way Mr. Winchester.” He began, his palms were beginning to sweat with nerves but he pressed on, “Honesty, I haven’t had much luck in the dating scene over the years, being a single father has made it hard. Most guys run the other way when they find out I have a kid, not wanting to be tied down. But not your son, no. I spent months getting to know him slowly as my Daughter’s student teacher, and he spent months getting to know my daughter every day.” He paused, taking a deep breath before he continued. “I’m not gonna lie, I was attracted to your son the first time I saw him. But yes, his age did give me reservations at first. I didn’t think someone his age would ever give me the time of day, especially since I have a kid. Not many guys my own age would even bother, never mind someone as young as him. But you know what? He didn’t care. It wasn’t a deal breaker for him. He decided to give me a chance anyway and never makes me feel bad when I have to put Bianca first, or when I have to cancel a date because I can’t find a babysitter. Do you know how many men I’ve dated my own age that I can say that about? None. Absolutely none. Your son has shown so much more maturity than anyone I’ve ever dated before. He may only be twenty-three, but he is an adult who can make his own decisions. And I count my lucky stars every day that he decided to be with me. To accept me, baggage and all. And I don’t care how long it takes, I will prove to you that his decision wasn’t a mistake, because your son is worth it, and I’m lucky to have him in my life.” Cas finished his speech, hands shaking and throat tight with emotion. He can see Dean gaping to his side, but he just stared at John, waiting for his reaction. The older man’s eyebrows have jumped to his hairline, probably having not expected Cas to speak so strongly, before Cas saw him smirk.

“Well, it’s good to know you feel so strongly about my son.” He remarked, and Cas thought he almost seems impressed.

“I do. I care about your son a lot. And I understand your concerns, but just know, I’d never do anything to hurt him.” He promised the man.

“Well, okay then. I’m gonna hold you to that. As long as you take good care of my boy, we won’t have any problems.” It might not be blatant approval, but Cas will take what he can get. His shoulders relaxed from where they had tensed up and he breathed out a sigh of relief.

“Okay, now that that is done with, why don’t we get going Cas. We still gotta drop Bee off to Gabe before it gets too late.” Dean chimes in, and Cas was happy for the change in conversation.

“Oh you guys going to spend some alone time together? Getting your freak on?” Sam teases from the other side of the room. Cas had forgotten he was still there, and his words send a blush to Cas’ face.

“Do you really want to know anything about my sex life?” Dean smirked, taunting his little brother.

“Nope. Nope we do not.” John quickly interjected as he got up from his chair. The rest of them stood as well and John held his hand out for Cas who took it.

“Remember what I said. And if you hurt my son, just know that I have no problem going to jail.” He threatened with a smile, making Cas gulp before responding. “Yes, sir.”

They corral Bianca from Mary and say their goodbyes before piling in the car. Cas made the quick drive over to Gabe’s house where he kissed his daughter goodbye, and then its just the two of them in the car. The silence is heated, both of then knowing where the night is about to lead.


	18. Chapter 18

Dean sat in the passenger seat of Cas’ car as Cas drove them back to his house. The anticipation of what they had planned was growing as they got closer to their destination. He had put it out of his mind during dinner; too focused on making sure everything went smoothly between his parents and his boyfriend. But now that he had nothing to distract his thoughts, he was a mess of emotions inside. He was definitely excited, thinking about going all the way with Cas; The thought of the older man pushing inside him for the first time had him chubbing up a bit inside of his jeans. He couldn’t deny that he was nervous though. He knew there was going to be some pain, but he trusted Cas to take care of him.

He had spent a long time in the shower earlier, before Cas had arrived at his house. He had made sure to clean himself thoroughly. He had even bought and used an enema to make sure he was squeaky clean. _That_ had been a weird experience that he really didn’t want to repeat any time soon. He shuddered as he recalled it. At least now he wasn’t worried about it being messy. One less thing to be nervous about was a plus in his book.

They pulled up into the driveway and Cas cut off the ignition, before he turned to look at Dean.

“I know what we planned for tonight. But you know we don’t have to do anything if you aren’t comfortable Dean.” Cas assured him, probably noticing the nervousness rolling off of Dean. Dean smiled and felt warmth spread through him at how thoughtful Cas always was. It eased some of his nerves and solidified that he definitely was ready for this.

“I know Cas. I want to though.” He assured Cas, smiling shyly at the older man.

They exited the car and made their way inside the house, where Cas hung up their coats.

“Would you like to sit out here on the couch for a little bit and relax first? Or would you like to lay down in bed now?” Cas asked, giving Dean the choice.

“I, uh…I think I wanna lay down now.” Dean replied nervously, but not wanting to draw this out any further. If he waited, he would just be a wreck the entire time. His nerves felt like a live wire right now.

“Okay, Dean.” Cas smiled as he led the way down the hall to the last room on the left. They entered and Dean’s palms began to sweat, and his heart began to race before Cas pulled him in and placed a gentle kiss to his forehead.

“Relax, sweetheart. I’ll take good care of you.” And Dean believed him. Believed the calming words Cas was saying, and believed the sincerity in his voice. He knew Cas would be gentle, and would take care of him, because he always did. He nodded and Cas smiled, before he captured Dean’s lips with his own; gentle and firm he pressed their mouths together as he guided Dean towards the queen size bed. Cas ran his hands up the back of Dean’s shirt, breaking the kiss long enough to pull the tee over Dean’s head, before he dove back in, his tongue demanding entrance that the younger man freely gave. 

Their tongues dance together, tangling and twisting, and Cas continued undressing Dean; First his pants, and then his briefs, leaving Dean completely bare and exposed. He stepped back and took his fill of the younger man, and Dean could see the hunger in his eyes. His cock was hard now, standing tall and proud and Dean tried to cover himself with his hand before Cas shook his head.

“Don’t. Let me see you.” He growled, sending shivers down Dean’s spine.

“I want to see you too.” Dean whined, and Cas gave him what he wanted. He watched the older man strip in front of him; His shirt first, then his lower half, and soon they were both naked and bare to each other; cocks flush and hard.

“Lay down on your stomach.” Cas instructed him softly and Dean gulped before complying; laying face down in the middle of the bed, before Cas had him lift his hips to put a pillow underneath him. The older man covered his body with his own, kissing his cheek before kissing his way down Dean’s back until he reached the swell of his ass. He grabbed both cheeks in his hands and pulled them apart, exposing the virgin hole between them. Dean clenched his eyes tight against the raw vulnerability he was feeling at being so exposed to the older man’s view.

“Relax, sweetheart. This part should feel good.” Dean tried to follow Cas’ command, taking a deep breath and letting his muscles go lax. He wasn’t expecting the wet tongue that was then pressed against his hole. He yelped and felt his whole body jump in surprise, and he heard Cas chuckle behind him.

“Shuddup.” He mumbled into the pillow, face heating with embarrassment.

“I’m sorry.” Cas said, not sounding the least bit like he actually was. “I didn’t mean to make you jump.”

“Yeah, well…I wasn’t expecting a tongue on my ass.” Dean grumbled, still trying to calm his body down.

“My apologies. I should have asked first. I would like to open you up with my tongue first before I stretch you with my fingers. May I do that Dean?” Cas asked, voice gravely with arousal. Dean felt his cock twitch where it was trapped below him.

“G-go for it.” He managed to squeak out through the tightness in his throat. He felt Cas pull his cheeks apart again, and his tongue swept a wide stripe across his tight hole. The feeling was incredible. He had seen enough rimming porn to know it was supposed to feel good, but this was unreal. Cas repeated the broad swipes of his tongue, making Dean shake as his hole was licked over and over. He couldn’t hold back the moan that left his lips as he felt the tongue press in gentle, just barely breaching his tight ring of muscles.

“F-fuck.” He whimpered as Cas began working his wet muscle inside of his ass, stretching him open, preparing him for more. He alternated deep pushes and quick flicks of his tongue, reducing Dean to a trembling mess.

“P-please Cas… please…I-I n-need more…” He begged, not even sure what he was asking for.

“Do you think you are ready for my fingers?” Cas asked as he massaged the firm globes of Dean’s ass.

“Y-yeah, give me ‘em.” Dean slurred, arousal making words hard at the moment. Cas leaned over to grab the lube from where it was sitting on the nightstand.

“Roll over for me Dean. I want to see your face to make sure I’m not hurting you.” Cas said softly, and Dean rolled over to look up at the man. “Spread your legs for me sweetheart.”

Dean blushed, but did as Cas said, spreading his legs wide to make room for his boyfriend. Cas scooted up and lifted Dean’s legs to rest on his thighs, shifting the pillow beneath Dean’s ass to prop him up better. Cas opened the bottle and squirted lube onto the fingers of his right hand, warming them between his fingers. He held Dean open with his other hand as he pressed a lubed finger to Dean’s hold. Dean’s heart started to race in anticipation of feeling a finger press inside of him for the first time.

“Have you ever fingered yourself sweetheart?” Cas asked as he rubbed the lube around Dean’s hole.

“N-no. I’ve n-never had anything in…inside me.” He stammered out, voice shaky with nerves and arousal.

“Okay then. Push out gently when I push in. It might burn a tiny bit the first time, but that should go away fast. I’m gonna take my time stretching you to make sure I don’t hurt you when I push my cock inside of you.” Cas explained and Dean felt his chest flush at the words; arousal battling with the awkwardness he was feeling about being spread out about to be fingered for the first time.

“I-I trust you Cas.” He whispered shyly; both of them sharing a small smile before he felt the first push of a finger enter his virgin hole. His whole body tensed at the feeling; his hole trying to resist the finger when he remembered his instructions. He pushed out and then felt Cas’ finger sink deeper till it was all the way inside. He gasped and his eyes squeezed shut tight at the slight burn. It was just like Cas said, not bad, just a bit uncomfortable. Cas held his finger there, letting Dean become accustomed to the finger, before he gently pulled back and thrust it back in.

“Ngh! F-fuck.” Dean moaned, the feeling so foreign, but it lit him up inside. Cas continued to work his finger in and out of Dean, stretching him until his rim began to relax. Cas curled his finger upward and Dean yelped as a jolt of intense pleasure rushed through him. That must be his prostate that was just hit. Cas hit it a few more times, making Dean shake with pleasure, before he felt a second finger begin working in alongside the first. He hissed at the stretch, and Cas rubbed a soothing hand up the inside of his thighs, shushing him as he gently worked him open.

By the time he had three fingers fucking into him, scissoring and stretching his rim, Dean was a blubbering mess. His cock was leaking pre-cum all over his soft belly, and he felt like he could explode at any minute. He felt Cas’ fingers retreat and he whined at the loss, feeling too empty after being full.

“I think you’re ready for my cock now.” Cas’ voice was deep and gravely, and Dean could hear the arousal of the other man clear as day. He heard the sound of the lube being rubbed over the man’s cock before he felt the blunt tip of it press against his hole. “Look at me sweetheart.”

Dean opened his eyes and looked into the pools of blue in front of him. Cas was smiling at him and Dean felt a surge of intense feelings flow through his body.

“I l-love you Cas.” He blurted out as he felt his eyes well up with emotion. He watched a look of shock pass over Cas’ face before it melted into one of awe.

“Oh, Sweetheart. I love you too.” Cas said as he leaned down and kissed Dean gently before pulling back to gaze into his eyes. Dean felt raw and flayed open. He loved this man so much, and knowing he was loved in return had a tear breaking free to roll slowly down his cheek.

“You gonna make love to me now Cas?” He shakily joked, trying to lighten the mood after their confession of love. Cas reached out a finger to catch the tear.

“Of course, my love.” He whispered gently and braced his hands on either side of Dean’s head, covering him with his warm body. Dean felt the first push of his cock break through his tight ring and he clenched his eyes tight. His arms reached up to wrap around his boyfriend’s neck, holding on tight as he felt himself being filled. Cas took his time working his cock inside of Dean, stopping every so often to let him adjust to the large girth inside of him. When he finally bottomed out, they both groaned at the feeling. Cas peppered Dean’s face with kisses, making sure to kiss away the few tears that had leaked out of the younger man’s eyes; Tears of love as well as pain as his ass had stretched. It had hurt, being filled with a cock for the first time, but Cas had stretched him well and the pain had been minimal; more a pinching burn than anything. There was also pleasure, at being filled for the first time and the sensitive nerves of his rim were alight with pleasure. It was overwhelming for Dean; accepting Cas inside him for the first time. He was embarrassed at the tears, but each time Cas kissed one away, he felt himself being soothed; his heart growing for the man inside him.

“M-move Cas.” He begged, needing to feel more. Cas pulled back slowly, until the head of his cock tugged on his rim, before he thrust back in again gently, making Dean moan at the glide of his cock. “F-fuck Cas” He moaned.

The older man slowly worked his cock in and out of Dean, his thrusts gentle at first, then gradually picking up as Dean begged for more. Dean’s cock was leaking profusely. He screamed when Cas angled just right and struck his prostate, hitting it over and over as Dean babbled incoherently. He held on tight as his ass was fucked, and soon he felt his balls begin to draw up, his orgasm right there.

“Fuck, Imma cum.” He groaned loudly, just before he felt ropes of come shoot out of his untouched dick and land all over his chest and belly. Cas fucked him through it, his thrusts becoming erratic before he followed Dean over the edge. He felt his insides being painted with Cas cum, and his dick twitched uselessly at the dirtiness of it all.

It could have been minutes, or hours later, when Cas finally pulled out and flopped onto his back, pulling Dean to cuddle on top of his chest as he wrapped his arms around the younger man. He kissed Dean’s forehead, sending warm feelings of love through the young man.

“How do you feel sweetheart?” Cas asked concerned. Dean shifted a bit and could feel the twinge in his ass; a reminder of what they just did.

“G-good. My ass hurts a little, but uh…not too bad. That was amazing Cas.” He whispered, still in awe that he just experienced all of that with someone who loved him and who he loved in return. His throat was tight with emotion and he clung tighter to Cas, never wanting to let go. “I love you.” He whispered again.

“I love you so much Dean. Thank you for giving me your body like that. You did amazing, Love.” Cas praised him and Dean tucked his face into the older man’s neck, face flush from Cas’ words.

They both lay there together, sated from their lovemaking as their breathing slowed down and they fell asleep wrapped in each other’s embrace.


	19. Chapter 19

Cas sat in the stands with Bee beside him, as they watched the students being called up by name, one-by-one. It was August, and Dean was finally graduating. He had ended up having to take a last-minute summer class so he was graduating at a later ceremony than originally planned. He also had a job lined up at an elementary school in their town. Not the one Bianca went to- they had offered him a job too- but he had decided that he didn’t want to work in a place that his boyfriend’s daughter attended. He had figured it could be awkward dating a dad of one of his students. Cas had laughed when Dean had told him it had been bad enough when he was just crushing on a dad of one of his students, and then he slapped Cas playfully when he reminded him of the DILF conversation from their first date.

Another school in the district had offered him a position though, and Dean had jumped at the chance. Come September, he would be teaching Kindergarten at South Bay Elementary School. Bianca had been disappointed that he wasn’t going to be teaching at her school, but seeing as Dean was over their house almost every other night, she saw him enough to keep her happy.

“I can’t believe my baby is graduating.” Mary said beside him, tears in her eyes as she watched her son on the field.

“He is going to be a great teacher.” Cas told her “You raised him to be a kind man.”

“Thanks Cas. I’m glad my boy has you now.” She squeezed his shoulder before turning back to the graduation ceremony.

Over the last four months, Cas and Mary had become very friendly. Once she had realized that Cas’ own mother had disowned him, she made it her mission to treat him like a son, and invited him and Bee over for dinner at least once a week. She had told him that it broke her heart that Bianca never got to experience having a grandma to love her, so she went out of her way to spoil his little girl. Bianca, of course, ate up all the attention she was now getting, and Cas had never seen her so happy. He felt so lucky that Dean had come into his life.

John was still distant though. He was civil to Cas, and never did or said anything outright that he didn’t like him, but Cas could tell that he was still leery about his son dating an older man. Cas couldn’t really blame him either so he just went out of his way to be nice to John, hoping he’d eventually earn his approval. Cas was thrown out of his thoughts by Mary nudging his shoulder.

“Dean’s next!” She yelled and he turned to the field to watch.

“Dean Winchester!” He heard on the loudspeaker and his watched his boyfriend stand up and make his way up to the stage. Dean shook hands with the people standing there and smiled for a picture. His whole family whooped and hollered, Cas included, and he saw Dean chuckle as he made his way back to his seat.

The rest of the ceremony went fast, since there were not many students after Dean and soon, they were all in the parking lot. Dean was roped into many pictures and hugs while Cas just watched with a fond smile, feeling so proud of him.

“Papa, are we going out to eat yet!” Bianca whined as she tugged on his sleeve. He was pretty impressed that she had sat through the entire graduation without complaining until now.

“Yes Bee. A couple of more minutes and we will be leaving honey.” He promised her as he pushed his way through the crowds of people to get to his boyfriend. Dean looked up and smiled at him before leaning in for a kiss that Cas was happy to provide.

“Heya Cas.” Dean beamed, looking adorable in his cap and gown.

“Hello Dean. Congratulations sweetheart.”

“Thanks babe.” Dean smiled.

“Bianca is getting impatient so I’m going to go ahead and drive over to the restaurant now. I’ll meet you there.” He told the younger man before leading his daughter back to the car and making the short drive over. They were going to Lily Flanigan’s in Babylon Village. Dean’s parents had rented a party room for his graduation celebration.

Cas arrived and they made their way inside, the hostess directed them to the correct room. A few guests had already arrived and Cas found an empty table for himself and Bianca. There were chips on the table, which was enough to entertain her until the guest of honor finally arrived ten minutes later.

The party was loud and fun, people drank and danced to the music playing. They ate delicious food and Bianca had a great time. Cas didn’t get to talk to Dean much, since he was constantly being pulled in different directions, everyone wanting to congratulate him on his graduation. Charlie sat with Cas for a while though and they chatted about all different things. They had both gotten close over the last few months as well, and Cas was incredibly grateful to the fiery red head. If it hadn’t been for her, Dean and him most likely wouldn’t be together right now. He owed so much to her.

Eventually the party died down and most of the guests had cleared. Dean was finally able to make his way over to Cas, and he plopped himself down in a chair and sighed.

“Man, I’m wiped.” He groaned making Cas chuckle.

“I bet.” He replied. “I’m so proud of you Dean.” He told his boyfriend sincerely, and Dean blushed at the praise.

“Thanks Cas.” He rubbed the back of his neck as he smiled shyly. “I can’t believe I’m finally gonna be a teacher though. With my own class and everything.”

“You’re gonna do great Dean. I have faith in you.”

“Yeah...heh…I’m gonna be super busy now though. Ya know, with the class planning and stuff. We might not get to see each other as often. That’s gonna suck.” Dean lamented. Cas reached into his pocket and clasped his fingers around the item he had hidden there.

“I’ve been thinking a lot about that Dean. And I…uh…I have a suggestion, or actually, I have a question for you.” He began nervously.

“What’s that?” Dean asked curiously, eyebrow raised in question.

Cas pulled the item out of his pocket and held his hand out for Dean to see. “I was wondering, if perhaps…. you’d consider, um…moving in with me?” He asked, heart racing in nervousness as he waited for the other man’s reaction. Dean stared at the key in Cas’ hand and Cas watched a myriad of emotions pass over his face; shock, awe, disbelief, and what looked like hope, before his lips curled up in a smile.

“You serious Cas? You really want me to move in with you?” He asked in disbelief, and Cas saw his eyes well up.

“Yes…if that’s something you want Dean. I’d um…I’d love for us to live together.” He barely got the words out before Dean leaped out of his chair and almost into Cas’ lap and attacked Cas’ face with kisses.

“Yes. Yes, yes yes.” Dean spoke between pecks to Cas’ cheeks, lips, and nose and the older man chuckled at his boyfriend’s antics. “God Cas. I was so bummed that we might not get to spend as much time together once I start teaching. But… _fuck_ …. I can’t believe this. Shit I’m so happy right now.” Dean kissed him right on the lips before jumping up from the table and yelling loud. “We’re moving in together!”

The remaining guests all whooped and cheered, making Cas blush but smile fondly. He couldn’t wait for the next Chapter of their story together.


	20. Chapter 20

** Epilogue **

_Two Years Later_

Cas let Bianca drag him around the Children’s Carnival, just like he had every year before, and he felt a strong sense of Déjà vu. Two years ago, he had been in this same spot, and he had no idea that day would change his life. He had no idea that he would end up meeting the love of his life that day, right at this very Carnival. He smiled as his daughter dragged him to yet another ride she wanted to go on.

The last two years had been absolutely amazing. Dean had moved in right after graduation, and although it had been an adjustment for everyone, it had mostly gone smoothly. John had protested the change in living arraignments, but Dean had told him it was not up to John because he was an adult. Mary had luckily been on their side so John had just sighed and relented, but made sure to let them know he wasn’t pleased. Thankfully, over the last two years, John had finally, _finally_ grown to accept Cas and they had a decent relationship now. It helped that Bee had him wrapped around her little finger. She’d just bat her eyelashes and get anything she wanted from the man. Cas was pretty sure he even saw a tear in the man’s eye that time she had slipped and called him grandpa. Everyone had frozen in shock at first, not knowing how to react, but then John had pulled her onto his lap and told her he would always be a grandpa to her, no matter what happened. That was the day Cas had truly felt like he had found a family of his own. He finally had people besides Gabe who had his back and who loved his daughter like their own.

He was brought out of his reminiscing by his phone buzzing and he pulled it out to read the text he received.

“Come on Bianca, it’s time to go to the dunk tank.” He told her, before pocketing his phone. They walked across the field to where the dunk tank was and got in line to wait. They didn’t have to wait long, and before he knew it, they were in the front of the line.

“Hey Cas!” Charlie beamed at him where she was manning the booth, just like she had been that time two years ago. “You ready for this?”

“As ready as I’m ever gonna be.” He told her, as the nerves began to set in. She pulled a special ball out from behind the table and handed it to Bianca.

“You know what to do with this right little lady?” She winked at Bianca who rolled her eyes.

“I’m not a little lady anymore Charlie.” She scoffed before the smile made its way back on her face. “And yes, I know what to do with it.” She winked back. Cas hoped everything went to plan.

******************

Dean sat on top of the platform in the dunk tank, waiting to be plunged into the water. Charlie had convinced him to volunteer again, and didn’t really give him an option to say no. He didn’t really mind though. In between being dunked, his mind wandered to when he sat in this very spot two years ago. He could not have predicted just how much that day would come to mean to him. It had been the first time he ever set eyes on Cas; the man he’d come to love more than anything else in the world. He couldn’t have imagined he’d also be blessed to have his little girl in his life. The little girl that he loved as if she was his own daughter. His life was so much brighter now that he had them in his life.

He was brought out of his thoughts by Charlie.

“Get your head out of the clouds, Winchester!” She yelled, making him laugh. That’s when he noticed whose turn it was. Cas stood with Bee and he waved to them. They waved back and he watched as Bee, instead of throwing the ball at the target, ran up to it and slammed it just like she had that first time, plunging him into the water below. He sputtered as he stood back up, wiping the water from his eyes. He was about to call them out for cheating again, but the words got caught in his throat. Kneeling on one knee was Cas, and Dean stood frozen, his brain not quite catching on yet.

“Dean, Dean, this is for you.” Bianca called from the side of the tank as she held out the baseball, she had used to dunk him. But when he took it from her, he realized it wasn’t actually a baseball, but rather just baseball shaped. It had a split around the middle and he opened the top before gasping; inside sat a beautiful platinum ring. He blinked a few times before looking back at Bianca.

“Will you marry my papa and be my other Daddy?” She asked, her smile wide. He felt a sob catch in his throat before his brain came back online. He quickly climbed out of the tank, slipping back in the water in his rush, before he managed to actually get out. He ran to where Bianca was standing next to Cas. Cas who was still down on one knee. He reached his hand out for Dean and grabbed Dean’s shaking hand in his.

“Dean, Sweetheart, two years ago we met here in this very spot. I had no idea just how much that day would change my life. I was…I was so lonely before you, and I didn’t even realize how much, until you filled that empty spot in my heart.” Dean could see Cas’ eyes tearing up to match his own. “You’ve welcomed us into your own family, and gave us something we’ve never had before. So now, I’d like to welcome you officially into ours. Dean, my love, will you do me the honor of marrying me, of becoming my husband, and giving My daughter another man to call her dad?” Dean’s lips were trembling as the tears flowed freely now and he just nodded his head, unable to even speak past the lump of emotions in his throat. Cas chuckled and took the ring out of the box before placing it on Dean’s left ring finger. He stood up and pulled Dean into a hug. “Thank you for making me the happiest man in the world” He whispered. “I Love you so much.”

“I L-love y-you too.” Dean choked out through tears of joy. He leaned up to place a kiss on his fiancé’s lips _. His fiancé_. Holy Crap!

He heard cheers from all of the people surrounding him, but he paid them no mind. The only people he cared about in this moment was the man in his arms and the little girl hugging his waist. They were his everything, his whole world. And they would be his future. He couldn’t think of a better place to be.

**Notes for the Chapter:**

> Thank you so much for reading! It's done. Im so happy to complete my first multichaptered fic. Thanks to all who have followed along, your comments kept me going. 💙💙💙
> 
> Also, I may decide to write some timestamps for this fic. If you have something you'd like to see let me know!


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